CA2879970A1 - Herbicidal compositions comprising 4-amino-3-chloro-5-fluoro-6-(4-chloro-2-fluoro-3-methoxyphenyl)pyridine-2-carboxylic acid or a derivative thereof and acetyl-coa carboxylase (accase) inhibitors - Google Patents

Abstract

Provided herein are synergistic herbicidal compositions containing (a) a compound of formula (I): 4-amino-3-chloro-5-fluoro-6- (4-chloro-2-fluoro-3-methoxyphenyl)pyridine-2-carboxylic acid or a derivative thereof, or an agriculturally acceptable salt or ester thereof and (b) an ACCase inhibitor, including, e.g., clethodim, clodinafop-propargyl, cyhalofop-R-butyl, diclofop-methyl, fenoxaprop-Pethyl, fluazifop-P-butyl, haloxyfop-R-methyl, metamifop, pinoxaden, profoxydim, quizalofop-P-ethyl, sethoxydim and tralkoxydim, provide synergistic weed control of undesirable vegetation in rice, cereals, wheat, barley, oats, rye, sorghum, com/maize, sugarcane, sunflower, oilseed rape, canola, sugar beet, soybean, cotton, pineapple, pastures, grasslands, rangelands, fallowland, turf, tree and vine orchards, aquatics, plantation crops, vegetables, industrial vegetation management (IVM) or rights of way (ROW).

Description

HERBICIDAL COMPOSITIONS COMPRISING 4-AMINO-3-CHLORO-5-FLUORO-6-(4-CHLORO-2-FLUORO-3-METHOXYPHENYL) PYRIDINE-2-CARBOXYLIC ACID OR A
DERIVATIVE THEREOF AND ACETYL-CoA CARBOXYLASE (ACCASE) INHIBITORS
Priority Claim This application claims the benefit of -United States provisional patent application number 61/675,103 filed on July 24, 2012 and United States patent application number 13/839,043 filed on March 15, 2013, the disclosure of each of which is incorporated herein by reference in its entirety.
Field Provided herein are 'herbicidal compositions comprising and methods of controlling undesirable vegetation utilizing (a) 4-amino-3-chloro-5-fluoro-6-(4-chloro-2-41-uoro-3--methoxyphenyOpyridine-2-carboxylic acid or an agriculturally acceptable ester or salt thereof and (b) an acetyl-CoA earboxylase (ACCase) inhibitor.
Background The protection of crops from weeds and other vegetation which inhibit crop growth is a constantly reclining problem in agriculture. To help combat this problem, researchers in the field of synthetic chemistry have produced an extensive variety of chemicals and chemical formulations effective in the control of such unwanted growth.
Chemical herbicides of many types have been disclosed in the literature and a large number are in commercial use. However, there remains a need for compositions and methods that are effective in controlling undesirable vegetation.
Summary A first embodiment includes herbicidal compositions, comprising: a herbicidally effective amount of (a) a compound of the formula (I) NH, Cl = µN:
/10 =

F
,0 (1) or an agriculturally acceptable salt or ester thereof: and (b) ACCase inhibitors, or a salt or ester thereof.
RECTIFIED (RULE 91) - ISA/US

A second embodiment includes a composition of according to the first embodiment, wherein (a) is a C1.4 alkyl or benzyl ester of compound (I).
A third embodiment includes a composition of according to the first embodiment wherein (a) is a benzyl ester of compound (1).
A fourth embodiment includes a composition of according to the first embodiment wherein (a) is the compound of formula (1), which is the carboxylic acid.
A fifth embodiment includes compositions of the first, second, third, or fourth embodiments, wherein (b) is selected from the group consisting of: clethodim, clodinafop-propargyl, cyhalotbp-R-butyl, diclofop-methyl, fenoxaprop-P-ethyl, fluazifop-P-butyl, haloxyfop-R-methyl, m.etamifop, pinoxaden, profoxydim., quizalofop-P-ethyl, sethoxydim or tralkoxydim.
A sixth embodiment includes a composition of the first embodiment, wherein(a) is the compound of formula (I) or an agriculturally acceptable benzyl ester and (b) is clethodim.
A seventh embodiment includes a composition of the first embodiment, wherein (a) is the compound of formula ( I) or an agriculturally acceptable benzyl ester and (b) is clodinafop-propargyl.
An eighth embodiment includes a composition of the first embodiment, wherein (a) is the compound of formula (I) or an agriculturally acceptable benzyl ester and (b) is cyhalofop-R-butyl.
A ninth embodiment includes a composition of the first embodiment, wherein (a) is the compound of formula (I) or an agriculturally acceptable benzyl ester and (b) is diclofop-methyl.
A tenth embodiment includes a composition of the first embodiment, wherein (a) is the compound of formula (1) or an agriculturally acceptable benzyl ester and (b) is fenoxaprop-P-ethyl.
An eleventh embodiment includes a composition of the first embodiment, wherein (a) is the compound of formula (1) or an agriculturally acceptable benzyl ester and (I)) is fluazifop-P-butyl.
A twelfth embodiment includes a composition of the first embodiment, wherein (a) is the compound of formula (1) or an agriculturally acceptable benzyl ester and (b) is haloxyfop-R-methyl.
A thirteenth embodiment includes a composition of the first embodiment, wherein (a) is the compound of formula (I) or an agriculturally acceptable benzyl ester and (b) is metamifop.

2 RECTIFIED (RULE 91) - ISA/US

A fourteenth embodiment includes a composition of the first embodiment, wherein (a) is the compound of formula (I) or an agriculturally acceptable benzyl ester and (b) is pinoxaden.
A fifteenth embodiment includes a composition of the first embodiment, wherein (a) is the compound of formula (I) or an agriculturally acceptable benzyl ester and (b) is profoxydim.
A sixteenth embodiment includes a composition of the first embodiment, wherein (a) is the compound of formula (I ) or an agriculturally acceptable benzyl ester and (b) is quizalofop-P-ethyl.
A seventeenth embodiment includes a composition of the first embodiment, wherein (a) is the compound of formula (I) or an agriculturally acceptable benzyl ester and (b) sethoxydim.
An eighteenth embodiment includes a composition of the first embodiment, wherein (a) is the compound of formula (I) or an agriculturally acceptable benzyl ester and (b) is tralkyoxydim.
A nineteenth embodiment includes composition according to the first through the eighteenth embodiments further comprising a herbicide safener.
A twentieth embodiment includes a composition according to the first embodiment wherein the ratios the compound of formula (I) or agriculturally acceptable salt or ester thereof to clethodim or an agriculturally acceptable salt or ester thereof, expressed in units of weight to weight (g to g), gaelha to gaiiha, or gae/ha to gaelha, are within the range of about 1:140 to about 9:1, from about 1:35 to about 2.2:1 and from about 1:9 to about 1:8.
A twenty-first embodiment includes a composition according to the first embodiment wherein the ratios the compound of formula (I) or agriculturally acceptable salt or ester thereof to clodinafop-propargyl or an agriculturally acceptable salt or ester thereof, expressed in units of weight to weight (g to g), gae/ha to gailha, or gae/ha to gae/ha, are within the range of about 1:40 to about 60:1, from about 1/6 to about 2:3 and from about 1:3 to about 1:4.
A twenty-second embodiment includes a composition according to the first embodiment wherein the ratios the compound of formula (I) or agriculturally acceptable salt or ester thereof to cyhalofop-R-butyl or an agriculturally acceptable salt or ester thereof, expressed in units of weight to weight (g to g), gae/ha to gaiiha, or gae/ha to gae/ha, are within the range of about 1:155 to about 6:1, from about 1:34 to about 1:2, from about 1:10 to about 1:70, 4:1, 0.5:1, 1:7 and about 1:9.

3 RECTIFIED (RULE 91) - ISA/US

A twenty-third embodiment includes a composition according to the first embodiment wherein the ratios the compound of formula (1) or agriculturally acceptable salt or ester thereof to diclofop-methyl or an agriculturally acceptable salt or ester thereof, expressed in units of weight to weight (g to g), gae/ha to gailha, or gae/ha to gae/ha, are within the range of about 1:560 to about 5:1, from about 1:140 to 1:9 and 1:35.
A twenty-fourth embodiment includes a composition according to the first embodiment wherein the ratios the compound of formula (1) or agriculturally acceptable salt or ester thereof to fenoxaprop-P-ethyl or an agriculturally acceptable salt or ester thereof, expressed in units of weight to weight (g to g), gae/ha to gailha, or gae/ha to gaelha, are within the range of about 1:170 to about 30:1, from about 1:16 to about 4:1, from about 0.4:1 to about 0.6:1, 0.25:1 and 0.6:1 and the crop safeners isoxadifen-methyl and mefenpyr-diethyl are incorporated into the product.
A twenty-fifth embodiment includes a composition according to the first embodiment wherein the ratios the compound of formula (1) or agriculturally acceptable salt or ester thereof to fluazifop-P-butyl or an agriculturally acceptable salt or ester thereof, expressed in units of weight to weight (g to g), gaelha to gai/ha, or gae/ha to gae/ha, are within the range of about 1:210 to about 3:1, from about 1:41 to 0.8:1 and from about 1:10 to about 1:5.
A twenty-sixth embodiment includes a composition according to the first embodiment wherein the ratios the compound of formula (I) or agriculturally acceptable salt or ester thereof to haloxyfop-R -methyl or an agriculturally acceptable salt or ester thereof, expressed in units of weight to weight (g to g), gae/ha to gai/ha, or gae/ha to gaeiha, are within the range of about 1:45 to about 10:1, from about 1:6 to about 1:5, from about 0.65:1 and about 1.3:1.
A twenty-seventh embodiment includes a composition according to the first embodiment wherein the ratios the compound of formula (1) or agriculturally acceptable salt or ester thereof to metamifop or an agriculturally acceptable salt or ester thereof, expressed in units of weight to weight (g to g), gae/ha to gaiTha, or gae/ha to gae/ha, are within the range of about 1:150 to about 6:1, from about 1:34 to about 10:1, from about 1:2 to about 0.64:1, 0.6:1, 1:1, 1:4, and 3:1.
A twenty-eighth embodiment includes a composition according to the first embodiment wherein the ratios the compound of formula (1) or agriculturally acceptable salt or ester thereof to pinoxaden or an agriculturally acceptable salt or ester thereof, expressed in units of weight to weight (g to g), gae/ha to gaila, or gae/ha to gae/ha, are within the range of about 1:3010 about 150:1, from about 1:12 to about 2:1, from about 1:3 to about 1:2,2:1 and 1:2.

4 SUBSTITUTE SHEET (RULE 26) A twenty-ninth embodiment includes a composition according to the first embodiment wherein the ratios the compound of formula (I) or agriculturally acceptable salt or ester thereof to profoxydim or an agriculturally acceptable salt or ester thereof, expressed in units of weight to weight (g to g), gaelha to gal/ha, or gae/ha to gae/ha, are within the range of about 1:70 to about 29:1, from about 1:23 to about 3:1, from about 3:1 to about 1:3, 0.35:1, 0.17:1,2.8:1 and 1,4:1.
A thirtieth embodiment includes a composition according to the first embodiment wherein the ratios the compound of formula (I) or agriculturally acceptable salt or ester thereof to quizalofop-P-ethyl or an agriculturally acceptable salt or ester thereof, expressed in units of weight to weight (g to g), gae/ha to gai/ha, or gae/ha to gae/ha, are within the range of about 1:100 to about 12:1, from about 1:8 to about 19:1, 5:1, 1.16:1, 0.6:1, 9:1, 2.33:1 and 1.2:1.
A thirty-first embodiment includes a composition according to the first embodiment wherein the ratios the compound of formula (I) or agriculturally acceptable salt or ester thereof to sethoxydim or an agriculturally acceptable salt or ester thereof, expressed in units of weight to weight (g to g), gaelha to gal/ha, or gaeiha to gaeiha, are within the range of about 1:70 to about 29:1, from about 1:62 to about 0.6:1, from about 13:1 to about 1:8.5, 1:7.7, 1:30.9,0.5:1 and 1:8.5.
A thirty-second embodiment includes a composition according to the first embodiment wherein the ratios the compound of formula (I) or agriculturally acceptable salt or ester thereof to tmlkoxydim or an agriculturally acceptable salt or ester thereof, expressed in units of weight to weight (g to g), gae/ha to gal/ha, or gaelha to gaelha, are within the range of about 1:38 to about 60:1, from about 1:40 to about 0.6:1, from about 1:10 to about 1:6.3, 1:3, 1:6 and 1:1.5.
A thirty-third embodiment includes any composition according to the first through the thirty-second embodiments that, further comprising an agriculturally acceptable adjuvant, and/or carrier and/or herbicide safener.
A thirty-fourth embodiment includes any composition according to the first through the thirty-third embodiments, wherein synergy between herbicides is determined by the Colby equation.
A thirty-fifth embodiment includes any composition according to the first embodiment wherein (b) is cyhalofop-butyl or carboxylic acid, carboxylate salt, or ester thereof, wherein the composition further comprises penoxsulam, bentazon-sodium, triclopyr, bispyribac-sodium, imazamox, benzobicyclon, quinclorac, glyphosate, glufosinate,

5 RECTIFIED (RULE 91) - ISA/US

benfuresate, fentrazamide, indanofan, ipfencarbazone, mefenacet, oxazichlomefone, pretilachlor, propyrisulfuron, pyraclonil, pyriftalid, or pyrimisulfan, or an agriculturally acceptable salt, carboxylic acid, carboxylate salt, or ester thereof, in combination as a synergistic 3 way/ternary mixture.
A thirty-sixth embodiment includes any composition according to the first embodiment wherein (b) is fenoxaprop, metamifop, or profoxydim, or agriculturally acceptable salt, ester, carboxylate salt, or carboxylic acid thereof, wherein the composition further comprises penoxsulam, bentazon-sodium, triclopyr, bispyribac-sodium, imazamox, benzobicyclon, quinclorac, glyphosate, glufosinate, benfuresate, fentrazamide, indanofan, ipfencarbazone, mefenacet, oxazichlomefone, pretilachlor, propyrisulfuron, pyraclonil, pyriftalid, or pyrimisulfan, or an agriculturally acceptable salt, carboxylic acid, carboxylate salt, or ester thereof, in combination as a synergistic 3 way/ternary mixture.
A thirty-seventh embodiment includes methods for controlling undesirable vegetation comprising the steps of contacting the vegetation or the locus thereof with or applying to the soil or water to prevent the emergence or growth of vegetation the at least one composition according to the first through the thirty-sixth embodiments.
A thirty-eighth embodiment includes methods for controlling undesirable vegetation comprising the steps of contacting the vegetation or the locus thereof with or applying to the soil or water to prevent the emergence or growth of vegetation utilizing a herbicidally effective amount of (a) a compound of the formula (I) CI
I
OH
Cl "'F 0 ,,0 (I) or an agriculturally acceptable salt or ester of thereof, and (b) an ACCase inhibitor.
A thirty-ninth embodiment includes methods of the thirty-seventh and thirty-eighth embodiments, wherein the undesirable vegetation is controlled in rice, cereals, wheat, barley, oats, rye, sorghum, corn/maize, sugarcane, sunflower, oilseed rape, canola, sugar beet, soybean, cotton, pineapple, pastures, grasslands, rangelands, fallowland, turf, tree and vine orchards, aquatics, plantation crops, vegetables, industrial vegetation management (IVM) or rights of way (ROW).

6 RECTIFIED (RULE 91) - ISA/US

7 A fortieth embodiment includes methods of the thirty-seventh and thirty-eighth embodiments wherein the undesirable vegetation is immature.
A forty-first embodiment includes methods of the thirty-seventh and thirty-eighth embodiments wherein the compounds (a) and (b) are applied to water.
A forty-second embodiment includes methods according to the forty-first embodiment, wherein the water is part of a flooded rice paddy.
A forty-third embodiment includes methods according to the thirty-seventh and thirty-eighth embodiments, wherein compounds (a) and (b) are applied pre-emergently to the weed or crop.
A forty-fourth embodiment includes methods according to the thirty-seventh and thirty-eighth embodiments, wherein compounds (a) and (b) are applied post-emergently to the weed or crop.
A forty-fifth embodiment includes methods according to the thirty-seventh and thirty-eighth embodiments, wherein the undesirable vegetation is controlled in glyphosate-, 5-enolpynivylshikimate-3-phosphate (EPSP) synthase inhibitor-, glufosinate-, glutamine synthetase inhibitor-, dicamba-, phenoxy auxin-, pyridyloxy auxin-, synthetic auxin-, auxin transport inhibitor-, aryloxyphenoxypropionate-, cyclohexanedione-, phenylpyrazoline-, acetyl CoA carboxylase (ACCase) inhibitor-, imidazolinone-, sulfonylurea-, pyrimidinylthiobenzoate-, triazolopyrimidine-, sulfonylaminocarbonyltriazolinone-, acetolactate synthase (ALS) or acetohydroxy acid synthase (AHAS) inhibitor-, 4-hydroxyphenyl-pyruvate dioxygenase (HPPD) inhibitor-, phytoene desaturase inhibitor-, carotenoid biosynthesis inhibitor-, protoporphyrinogen oxidase (PPO) inhibitor-, cellulose biosynthesis inhibitor-, mitosis inhibitor-, microtubule inhibitor-, very long chain fatty acid inhibitor-, fatty acid and lipid biosynthesis inhibitor-, photosystem I
inhibitor-, photosystem 11 inhibitor-, triazine-, or bromoxynil- tolerant crops.
A forty-sixth embodiment includes methods according to the forty-fifth embodiment, wherein the resistant or tolerant crop possesses multiple or stacked traits conferring resistance or tolerance to multiple herbicides or multiple modes of action.
A forty-seventh embodiment includes methods according to the thirty-seventh and thirty-eighth embodiments, wherein the undesirable vegetation comprises a herbicide resistant or tolerant weed.
A forty-eighth embodiment includes methods according to the forty-seventh embodiment, wherein the resistant or tolerant weed is a biotype with resistance or tolerance RECTIFIED (RULE 91) - ISA/US

to multiple herbicides, multiple chemical classes, or multiple herbicide modes-of-action or via multiple resistance mechanisms.
A forty-ninth embodiment includes methods according to the forty-seventh embodiment wherein the resistant or tolerant weed is a biotype resistant or tolerant to azetolactate synthase (ALS) or acetohydroxy acid synthase (AHAS) inhibitors, photosystem II inhibitors, acetyl CoA carboxylase (ACCase) inhibitors, synthetic auxins, auxin transport inhibitors, photosystem I inhibitors, 5-enolpyruvylshilcimate-3-phosphate (EPSP) synthase inhibitors, microtubule assembly inhibitors, fatty acid and lipid synthesis inhibitors, protoporphyrinogen oxidase (PPO) inhibitors, carotenoid biosynthesis inhibitors, very long chain fatty acid (VLCFA) inhibitors, phytoene desaturase (PDS) inhibitors, glutamine synthetase inhibitors, 4-hydroxyphenyl-pyruvate-dioxygenase (HPPD) inhibitors, mitosis inhibitors, cellulose biosynthesis inhibitors, herbicides with multiple modes-of-action, quinclorac, arylaminopropionic acids, diknzoquat, endothall, or organoarsenicals.
A fiftieth embodiment includes the composition according to any of embodiments 4, wherein the ratio of compound (a) to compound (b) is such that the composition exhibits synergy.
A fifty-first embodiment includes the composition according to any of embodiments 1-4 or 50, wherein the weight ratio of the compound of formula (1) or agriculturally acceptable salt or ester thereof to clethodim or agriculturally acceptable salt or ester thereof is from about 1:140 to about 9:1.
A fifty-second embodiment includes the composition according to any of embodiments 1-4 or 50, wherein the weight ratio of the compound of formula (I) or agriculturally acceptable salt or ester thereof to clodinafop-propargyl or agriculturally acceptable salt or ester thereof is from about 1:40 to about 60:1.
A fifty-third embodiment includes the composition according to any of embodiments 1-4 or 50, wherein the weight ratio of compound of formula (r) or agriculturally acceptable salt or ester thereof to cyhalofop-R-butyl or agriculturally acceptable salt or ester thereof is from about 1:155 to about 6:1.
A fifty-fourth embodiment includes the composition according to any of embodiments 1-4 or 50, wherein the weight ratio of the compound of formula (r) or agriculturally acceptable salt or ester thereof to diclofop-methyl or agriculturally acceptable salt or ester thereof is from about 1:560 to about 5:1.
A fifty-fifth embodiment includes the composition according to any of embodiments 1-4 or 50õ wherein the weight ratio of the compound of formula (I) or agriculturally

8 RECTIFIED (RULE 91) - ISA/US

acceptable salt or ester thereof to fenoxaprop-P-ethyl of agriculturally acceptable salt or ester thereof is from about 1:170 to about 30:1, and the crop safeners isoxadifen-methyl and mefenpyr-diethyl are incorporated into the product A fifty-sixth embodiment includes the composition according to any of embodiments 1-4 or 50, wherein the weight ratio of the compound of formula (1) or agriculturally acceptable salt or ester thereof to fluazifop-P-butyl or agriculturally acceptable salt or ester thereof is from about 1:210 to about 3:1.
A fifty-seventh embodiment includes the composition according to any of embodiments 1-4 or 50, wherein the weight ratio of the compound of formula (I) or agriculturally acceptable salt or ester thereof to haloxyfop-R-methyl or agriculturally acceptable salt or ester thereof is from about 1:45 to about 10:1.
A fifty-eighth embodiment includes the composition according to any of embodiments 1-4 or 50, wherein the weight ratio of the compound of formula (I) or agriculturally acceptable salt or ester thereof to metamifop or agriculturally acceptable salt or ester thereof is from about 1:150 to about 6:1.
A fifty-ninth embodiment includes the composition according to any of embodiments 1-4 or 50, wherein the weight ratio of the compound of formula (I) or agriculturally acceptable salt or ester thereof to pinoxaden or agriculturally acceptable salt or ester thereof is from about 1:30 to about 150:1.
A sixtieth embodiment includes the composition according to any of embodiments 4 or 50, wherein the weight ratio of the compound of formula (1) or agriculturally acceptable salt or ester thereof to profoxydim or agriculturally acceptable salt or ester thereof is from about 1:70 to about 29:1.
A sixty-first embodiment includes the composition according to any of embodiments 1-4 or 50. wherein the weight ratio of the compound of formula (1) or agriculturally acceptable salt or ester thereof to quizalofop-P-ethyl or agriculturally acceptable salt or ester thereof is from about 1:100 to about 12:1.
A sixty-second embodiment includes the composition according to any of embodiments 1-4 or 50, wherein the weight ratio of the compound of formula (1) or agriculturally acceptable salt or ester thereof to sethoxydim or agriculturally acceptable salt or ester thereof is from about 1:70 to about 29:1.
A sixty-third embodiment includes the composition according to any of embodiments 1-4 or 50, wherein the weight ratio of the compound of formula (1) or agriculturally

9 RECTIFIED (RULE 91) - ISA/US

acceptable salt or ester thereof to tralkoxydim or agriculturally acceptable salt or ester thereof is from about 1:38 to about 60:1.
Provided herein are herbicidal compositions comprising a methods of controlling undesirable vegetation utilizing a herbicidally effective amount of (a) a compound of the formula (I.).
NH, Cl . 0 (I) or an agriculturally acceptable salt or ester of thereof, and (b) an ACCase inhibitor.
Exemplary A.CCase inhibitors include, but are not limited to, clethodim, clodinafop-propargyl, cyhalofop-R-butyl, diclofop-rriethyl, fenoxaprop-P-ethyl, fluazifop-P-butyl, haloxyfop-R-methyl, metamifop, pinoxaden, profoxydim, quizalofop-P-ethyl, sethoxydim or tralkoxydim. The compositions may also contain an agriculturally acceptable adjuvant or carrier.
Detailed Description DEFINITIONS
As used herein, the compound of formula (I) has the following structure:

Cl =

CI
(11-1) fi3C
The compound of formula (I) can be identified by the name 4-amino-3-chloro-6-(4-chloro-2-fluoro-3-methoxypheny1)-5-fluoropyridine-2-carboxylic acid and has been described in U.S.
Patent 7,314,849 (B2), which is incorporated herein by reference in its entirety. Exemplary uses of the compound of the formula (I) include controlling undesirable vegetation, including grass, broadleaf and sedge weeds, in multiple non-crop and cropping situations.
RECTIFIED (RULE 91) - ISA/US

Without being limited to any theory, ACCase inhibitors believed to inhibit to any extent acetyl coenzyme A carboxylase (ACCase), an enzyme involved in fatty acid synthesis.
Exemplary ACCase inhibitors include, but are not limited to aiyloxyphenoxy propionates an.d the cyclohexanediones. Further examples include, but are not limited to, clethodim, clodinafop-propargyl, cyhalofop-R-butyl, diclofop-methyl, fenoxaprop-P-ethyl, fluazifop-P-butyl, haloxyfbp-R-methyl, metamifop, pinoxaden, profoxydim, quizalofop-P-ethyl, sethoxydim and tralkoxydim.
As used herein, clethodim is 241-[[[(2E)-3-chloro-2-propen-1 -yl]oxyjiiminoipropyl]-542-(ethylthio)propyl]-3-hydroxy-2-cyclohexen- I -one and possesses the following structure:

CH- , SOH

This compound is described in Tomlin, C., ed. A World Compendium The Pesticide Manual. 15th ed. Alton: BCPC Publications, 2009 (hereafter "The Pesticide Manual, Fifteenth Edition, 2009."). Exemplary uses of clethodim include its use as a herbicide for, e.g., post-emergence control of annual and perennial grasses in broadleaf crops, vegetables, trees and vines.
As used herein, clodinafop-propargyl is 2-propynyl (2R)-244-[(5-chloro-3-fluoro-2-pyridinyl)oxy]phenoxy]propanoate and possesses the following structure:

Cl F

This compound is described in The Pesticide Manual, Fifteenth Edition, 2009.
Exemplary uses of clodinafop-propargyl include its use as a herbicide for, e.g., post-emergence control of annual grasses, including, e.g., Avena, Lolium, Setaria, Phalaris and Alopecurus spp., in cereals.
As used herein, cyhalofop-butyl is butyl (2R)-244-(4-cyano-2-fluorophenoxy)phenoxyipropanoate and possesses the following structure:

SUBSTITUTE SHEET (RULE 26) This compound is described in The Pesticide Manual, Fifteenth Edition, 2009.
Exemplary uses of cyhalotbp-butyl include its use as a herbicide for, e.g., post-emergence control of annual and perennial grass weeds in seeded and transplanted rice.
As used herein, diclofop-methyl is methyl 244(2,4-dichlorophenoxy)phenoxy]propanoate and possesses the following structure:

CI CI Oyk0õC1-13 This compound is described in The Pesticide Manual, Fifteenth Edition, 2009.
Exemplary uses of diclofop-methyl include its use as a herbicide for, e.g., post-emergence control of wild oats, wild millets, and other annual grass weeds in wheat, barley, lye, red fescue, and broadleaf crops.
As used herein, fen.oxaprop-P-ethyl is ethyl (2R)-244-[(6-chloro-2-benzoxazoly0oxy]phenoxy]propanoate and possesses the following structure:
CI

K)-\
Oyt, 11.1 CH3 This compound is described in The Pesticide Manual, Fifteenth Edition, 2009.
Exemplary uses of fenoxaprop-P-ethyl include its use as a herbicide for, e.g., control of annual and perennial grass weeds in crops including rice.
As used herein, fluazifop-P-butyl is butyl (2R)-244-[[54trifluoromethyl)-2-pyridinyl]oxy]phenoxyipropanoate and possesses the following structure:

,N)L, This compound is described in The Pesticide Manual, Fifteenth Edition, 2009.
Exemplary uses of fluazifop-P-butyl include its use as a herbicide for, e.g., post-emergence SUBSTITUTE SHEET (RULE 26) control of wild oats, volunteer cereals, and annual and perennial grass weeds in oilseed rape, sugar beet, fodder beet, potatoes, vegetables, cotton, soya beans, pome fruit, stone fruit, bush fruit, vines, citrus fruit, pineapples, bananas, strawberries, sunflowers, alfalfa, coffee, ornamentals and other broadleaf crops. Fluazifop-P-butyl can be used in combination with safeners, e.g., isoxadifen-ethyl or tnefenpyr-diethyl.
As used herein, haloxyfop-P-methyl is methyl (2R)-2-[44[3-chloro-5-(trifluoromethyl)-2-pyridinytioxy]phenoxy]propanoate and possesses the following structure:

FiC ..7,...õ

Ci This compound is described in The Pesticide Manual, Fifteenth Edition, 2009.
Exemplary uses of haloxyfop-P-methyl include its use as a herbicide for, e.g., post-emergence control of annual and perennial grasses in a variety of crops.
As used herein, metarnifop is (2R)-2-P-[(6-chloro-2-benzoxazoly1)oxy]phenoxy]-N-(2-fluoropheny1)-N-methylpropanamide and possesses the following structure:
Cl -------' 1 \ / 0 7' -V-----0 CH3 Cl-I3 F
This compound is described ia The Pesticide Manual, Fifteenth Edition, 2009.
Exemplary uses of metamifo-p include its use as a herbicide for, e.g., post-emergence control of annual and perennial grasses in a variety of crops, including rice.
As used herein, pinoxaden is 8-(2,6-diethy1-4-methylpheny0-1,2,4,5-tetrahydro-oxo-7H-pyrazolo[1,2-d][1,4.5]oxadiazepin-9-yi 2,2-dimethylpropanoate and possesses the following structure:

0 .
/'----NN--- =
0 \ i CH3 \ N' / \ ir -.....-0 \

CH,, HC cH3 -SUBSTITUTE SHEET (RULE 26) This compound is described in The Pesticide Manual, Fifteenth Edition, 2009.
Exemplary uses of pinoxaden include its use as a herbicide for, e.g., post-emergence control of annual grasses, including Alopecurus, Apera, Avena, Lolium, .Phalaris and Setaria sppe in wheat and barley.
As used herein, profoxyditn is 2-[1-[[2-(4-chlorophenoxy)propoxy]imino]butyl]-hydroxy-5-(tetranydro-211-thiopyran-3-y1)-2-cyclohexen- I-one and possesses the following structure:
Cl CHOH
This compound is described in The Pesticide Manual, Fifteenth Edition, 2009.
Exemplary uses of profoxydim include its use as a herbicide for, e.g., control of grass weeds in rice.
As used herein, quizalofop-P-ethyl is ethyl (2R)-2-114-[(6-chloro-2-quinoxalinyl)oxy]phenoxy]propanoate and possesses the following structure:

0,171-e, This compound is described ia The Pesticide Manual, Fifteenth Edition, 2009.
Exemplary uses of quizalofop-P-ethyl include its use as a herbicide for, e.g., selective post-emergence control of annual and perennial grass weeds in crops.
As used herein, sethoxydiM is 2-[l -(ethoxyimino)buty1]-542-(ethylthio)propyll-hydroxy-2-cyclohexen-1-one and possesses the following structure:

SUBSTITUTE SHEET (RULE 26) OH

This compound is described in The Pesticide Manual, Fifteenth Edition, 2009.
Exemplary uses of sethoxydim include its use as a herbicide for, e.g., control of annual and perennial grasses in broadleaf crops.
As used herein, tmlkoxydim is 241-(ethoxyimino)propy1]-3-hydroxy-5-(2,4,6-trimethylpheny1)-2-eyclohexen-1-one and possesses the following structure:
, '7"-CH3 CH3 OH u This compound is described in The Pesticide Manual, Fifteenth Edition, 2009.
Exemplary uses of tralkoxydim include its use as a herbicide for, e.g., post-emergence control of annual grass weeds in wheat and barley.
As used herein, herbicide means a compound, e.g., active ingredient that kills, controls or otherwise adversely modifies the growth of plants.
As used herein, a herbicidally effective or vegetation controlling amount is an amount of active ingredient which causes an adversely modifying effect to the vegetation e.g., causing deviations from natural development, killing, effecting regulation, causing desiccation, causing retardation, and the like.
As used herein, controlling undesirable vegetation means preventing, reducing, killing, or otherwise adversely modifying the development of plants and vegetation.
Described herein are methods of controlling undesirable vegetation through the application of certain herbicide combinations or compositions. Methods of application include, but are not limited to applications to the vegetation or locus thereof, e.g., application to the area adjacent to the vegetation, as well as preemergence, postemergence, foliar (broadcast, directed, banded, spot, mechanical, over-the-top, or rescue), and in-water applications (emerged and submerged vegetation, broadcast, spot, mechanical, water-injected, granular broadcast, granular spot, shaker bottle, or stream spray) via hand, backpack, machine, tractor, or aerial (airplane and helicopter) application methods..
SUBSTITUTE SHEET (RULE 26) As used herein, plants and vegetation include, but are not limited to, germinant seeds, emerging seedlings, plants emerging from vegetative propagules, immature vegetation, and established vegetation.
As used herein, agriculturally acceptable salts and esters refer to salts and esters that exhibit herbicidal activity, or that are or can be converted in plants, water, or soil to the referenced herbicide. Exemplary agriculturally acceptable esters are those that are or can be hydrolyzed, oxidized, metabolized, or otherwise converted, e.g., in plants, water, or soil, to the corresponding carboxylic acid which, depending on the pH, may be in the dissociated or undissociated form.
Exemplary salts include those derived from alkali or alkaline earth metals and those derived from ammonia and amines. Exemplary cations include sodium, potassium, magnesium, and aminium cations of the formula:
RIR2R3R4N+
wherein RI, R2, R3 and R.4 each, independently represents hydrogen or C1-C12 alkyl, C3-C12 alkenyl or C3-C12 allcynyl, each of which is optionally substituted by one or more hydroxy, C1-C4 alkoxy, C1-C4 alkylthio or phenyl groups, provided that RI, R2, R3 and R4 are sterically compatible. Additionally, any two of RI, R2, R3 and le together may represent an aliphatic difunctional moiety containing one to twelve carbon atoms and up to two oxygen or sulfur atoms. Salts can be prepared by treatment with a metal hydroxide, such as sodium hydroxide, with an amine, such as ammonia, trimethylamine, diethanolamine, 2-methylthiopropylamine, bisallylamine, 2-butoxyethylamine, motpholine, cyclododecylamine, or benzylamine or with a tetraalkylammonium hydroxide, such as tetramethylammonium hydroxide or choline hydroxide.
Exemplary esters include those derived from CI-Cu alkyl, C3-C19 alkenyl, C3-alkynyl or C7-C10 aryl-substituted alkyl alcohols, such as methyl alcohol, isopropyl alcohol, 1-butanol, 2-ethylhexanol, butoxyethanol, methoxypropanol, allyl alcohol, propargyl alcohol, cyclohexanol or tmsubstituted or substituted benzyl alcohols. Benzyl alcohols may be substituted with from 1-3 substituents independently selected from halogen, C1-C4 alkyl or alkoxy. Esters can be prepared by coupling of the acids with the alcohol using any number of suitable activating agents such as those used for peptide couplings such as dicyclohexylcarbodiimide (DCC) or carbonyl diimidazole (CDI); by reacting the acids with alkylating agents such as alkylhalides or alkylsulfonates in the presence of a base such as triethylamine or lithium carbonate; by reacting the corresponding acid chloride of an acid SUBSTITUTE SHEET (RULE 26) with an appropriate alcohol; by reacting the corresponding acid with an appropriate alcohol in the presence of an acid catalyst or by transesterification.
COMPOSITIONS AND METHODS
Provided herein are herbicidal compositions comprising a herbicidally effective amount of (a) a compound of the formula (1) N H, CI r ,0 (I) HC
or an agriculturally acceptable salt or ester of thereof, and (b) an ACCase inhibitor. in certain embodiments, the ACCase inhibitor is clethodim, clodinafop-propargyl, cyhalofop-R-butyl, diclofop-methyl, fenoxaprop-P-ethyl, fluazifop-P-butyl, haloxyfop-R-methyl, metamifop, pinoxaden, profoxydim, quizalofop-P-ethyl, sethoxydim or tralkoxydim or derivative thereof, e.g., salt, carboxylic acid, carboxylate salt, or ester thereof.
Provided herein are also methods of controlling undesirable vegetation comprising contacting the vegetation or the locus thereof, i.e., are adjacent to the vegetation, with or applying to the soil or water to prevent the emergence or growth of vegetation a herbicidally effective amount of the compound of formula (I) and (b) an ACCase inhibitor.
In certain embodiments, the methods employ the compositions described herein.
Furthermore, in some embodiments, the combination of compound (I) or agriculturally acceptable salt or ester thereof and ACCase inhibitors, or an agriculturally acceptable salt or ester thereof exhibits synergism, e.g., the herbicidal active ingredients are more effective in combination than when applied individually. Synergism has been defined as '"an interaction of two or more factors such that the effect when combined is greater than the predicted effect based on the response of each factor applied separately."
Senseman, S., ed. Herbicide Handbook. 9th ed. Lawrence: Weed Science Society of America, 2007. In certain embodiments, the compositions exhibit synergy as determined by the Colby's equation. Colby, S.R. 1967. Calculation of the synergistic and antagonistic response of herbicide combinations. Weeds 15:20-22.

SUBSTITUTE SHEET (RULE 26) In certain embodiments of the compositions and methods described herein, the compound of formula (1), i.e., the carboxylic acid, is employed. In certain embodiments, a carboxylate salt of the compound of formula (I) is employed. In certain embodiments, an aralkyl or alkyl ester is employed. In certain embodiments, a benzyl, substituted benzyl, or Cm alkyl, e.g., n-butyl ester is employed. In certain embodiments, the benzyl ester is employed.
In some embodiments, the compound of formula (I) or salt or ester thereof and ACCase inhibitor are formulated in one composition, tank mixed, applied simultaneously, or applied sequentially.
Herbicidal activity is exhibited by the compounds when they are applied directly to the plant or to the locus of the plant at any stage of growth. The effect observed depends upon the plant species to be controlled, the stage of growth of the plant, the application parameters of dilution and spray drop size, the particle size of solid components, the environmental conditions at the time of use, the specific compound employed, the specific adjuvants and carriers employed, the soil type, and the like, as well as the amount of chemical applied. These and other factors can be adjusted to promote non-selective or selective herbicidal action. In some embodiments, the compositions described herein are applied as a post-emergence application, pre-emergence application, or in-water application to flooded paddy rice or water bodies (e.g., ponds, lakes and streams), to relatively immature undesirable vegetation to achieve the maximum control of weeds.
In some embodiments, the compositions and methods provided herein are utilized to control weeds in crops, including but not limited to direct-seeded, water-seeded and transplanted rice, cereals, wheat, barley, oats, rye, sorghum, corn/maize, sugarcane, sunflower, oilseed rape, canola, sugar beet, soybean, cotton, pineapple, pastures, grasslands, rangelands, fallowland, turf, free and vine orchards, aquatics, plantation crops, vegetables, industrial vegetation management (IVM) and rights of way (ROW).
In certain embodiments, the compositions and methods provided herein are utilized to control weeds in rice. In certain embodiments, the rice is direct-seeded, water-seeded, or transplanted rice.
The compositions and methods described herein may be used to control undesirable vegetation in glyphosate-tolerant-, 5-enolpytuvylshikimate-3-phosphate (EPSP) synthase inhibitor-tolerant-, glufosinate-tolerant-, glutamine synthetase inhibitor-tolerant-, dicamba-SUBSTITUTE SHEET (RULE 26) tolerant-, phenoxy auxin-tolerant-, pyridyloxy auxin-tolerant-, auxin-tolerant-, auxin transport inhibitor-tolerant-, aryloxyphenoxypropionate-tolerant-, cyclohexanedione-tolerant-, phenylpyrazoline-tolerant-, acetyl CoA carboxylase (ACCase) inhibitor-tolerant-, imidazolinone-tolerant-, sulfonylurea-tolerant-, pyrimidinylthiobenzoate-tolerant-, triazolopyrimidine-tolerant-, sulfonylaminocarbonyltriazolinone-tolerant-, triazolopyrimidine-tolerant-, sulfonylaminocarbonyltriazolinone-tolerant-, acetolactate synthase (ALS) or acetohydroxy acid synthase (AHAS) inhibitor-tolerant-, 4-hydroxyphenyl-pyruvate dioxygenase (HPPD) inhibitor -tolerant-, phytoene desaturase inhibitor-tolerant-, carotenoid biosynthesis inhibitor-tolerant-, protoporphyrinogen oxidase (PPO) inhibitor -tolerant-, cellulose biosynthesis inhibitor-tolerant-, mitosis inhibitor-tolerant-, microtubule inhibitor-tolerant-, very long chain fatty acid inhibitor-tolerant-, fatty acid and lipid biosynthesis inhibitor-tolerant-, photosystem I inhibitor-tolerant-, photosystem 11 inhibitor-tolerant-, triazine-tolerant- and bromoxynil-tolerant- crops (such as, but not limited to, soybean, cotton, canola/oilseed rape, rice, cereals, corn, sorghum, sunflower, sugar beet, sugarcane, turf, etc.), for example, in conjunction with glyphosate, EPSP
synthase inhibitors, glufosinate, glutamine synthase inhibitors, dicamba, phenoxy auxins, pyridyloxy auxins, synthetic auxins, auxin transport inhibitors, aryloxyphenoxypropionates, cyclobexanediones, phenylpyrazolines, ACCase inhibitors, imidazolinones, sulfonylureas, pyrimidinylthiobenzoates, dimethoxy-pyrimidines, triazolopyrimidine sulfonamides, sultbnylaminocarbonyltriazolinones, ALS or AHAS inhibitors, HPPD inhibitors, phytoene desaturase inhibitors, carotenoid biosynthesis inhibitors, PPO inhibitors, cellulose biosynthesis inhibitors, mitosis inhibitors, microtubule inhibitors, very long chain fatty acid inhibitors, fatty acid and lipid biosynthesis inhibitors, photosystem I
inhibitors, photosystem 11 inhibitors, PPO inhibitors, triazines, and bromoxynil The compositions and methods may be used in controlling undesirable vegetation in crops possessing multiple or stacked traits conferring tolerance to multiple chemistries and/or inhibitors of multiple modes of action. In some embodiments, the compound of formula (1) or salt or ester thereof and complementary herbicide or salt or ester thereof are used in combination with herbicides that are selective for the crop being treated and which complement the spectrum of weeds controlled by these compounds at the application rate employed. In some embodiments, the compositions described herein and other complementary herbicides are applied at the same time, either as a combination formulation, tank mix or sequentially.
The compositions and methods may be used in controlling undesirable vegetation in crops possessing agronomic stress tolerance (including but not limited to drought, cold, heat, SUBSTITUTE SHEET (RULE 26) salt, water, nutrient, fertility, pH), pest tolerance (including but not limited to insects, fungi and pathogens) and crop improvement traits (including but not limited to yield; protein, carbohydrate, or oil content; protein, carbohydrate, or oil composition; plant stature and plant architecture).
The compositions and methods provided herein are utilized to control undesirable vegetation. Undesirable vegetation includes, but is not limited to, undesirable vegetation that occurs in rice, cereals, wheat, barley, oats, rye, sorghum, corn/maize, sugarcane, sunflower, oilseed rape, canola, sugar beet, soybean, cotton, pineapple, range and pasture, grasslands, fallowland, turf, tree and vine orchards, aquatics, plantation crops, vegetables, industrial vegetation management (IVM) and rights of way (ROW).
In some embodiments, the methods provided herein are utilized to control undesirable vegetation in rice. In certain embodiments, the undesirable vegetation is Brachiaria platyphylla (Groseb.) Nash or (frockloa platyphylla (Nash) R.D. Webster (broadleaf signalgrass, BRAPP), Digitaria sanguinalis (L.) Scop. (large crabgrass, DIGSA), Echinochloa species (ECHSS), Echinochloa crus-galli (L.) P. Beauv.
(bamyardgrass, ECHCG), Echinochloa crus-pavonis (Kunth) Schult. (gulf cockspur, ECHCV), Echinochloa colonum (L.) LINK (junglerice, ECHCO), Echinochloa otyzoides (Ard.) Fritsch (early watergrass, ECHOR), Echinochloa olyzicola (Vasinger) .Vasinger (late watergrass, ECHPH), Echinochloa phyllopogon (Stapf) Koso-Pol. (rice bamyardgrass, ECHPH), Echinochloa polystachya (Kunth) Hitchc. (creeping river grass, ECHPO), Ischaemum rugosum Salisb.
(saram.ollagrass, ISCR.U), Leptochloa chinensis (L.) Nees (Chinese spran.gletop, LEFCH), Leptochloa fascicularis (Lam.) Gray (bearded sprangletop, LEFFA), Leptochloa panicoides (Presl.) Hitchc. (Amazon sprangletop, LEFPA), Otyza species (red and weedy rice, ORYSS), Panicum dichotomiflorum (L.) Michx. (fall panicum, PANDI), Paspalum dilatatum Poir.
(dallisgrass, PASDI), Rottboellia cochinchinensis (Lour.) W.D. Clayton (itchgrass, ROOEX), Cyperus species (CYPSS), Cyperus aqfformis L. (smallflower flatsedge, CYPDI), Cyperus dubius Rottb. (MAPDU), Cyperus esculentus L. (yellow nutsedge, CYPES), Cyperus iria L.
(rice flatsedge, CYPIR), Operus rotundus L. (purple nutsedge, CYPRO), Cyperus serotinus ROTTBIC.B.Clarke (CYPSE), Eleocharis species (ELOSS), Fimbristylis miliacea (L.) Vahl (globe fiingerush, FIMMI), Schoenoplectus species (SCPSS), Schoenoplectus juncoides Roxb. (Japanese bulrush, SCPJU), Bolboschoenus maritimus (L.) Palla or Schoenoplectus maritimus L. Lye (sea clubrush, SCPMA), Schoenoplectus mucronatus L.
(ricefield bulrush, SCPMU), Aeschynomene species, (jointvetch, AESSS), Alternanthera philoxeroides (Mart.) Griseb. (alligatorweed, ALRPH), Alisma plantago-aquatica L. (common waterplantain, SUBSTITUTE SHEET (RULE 26) ALSPA), Amaranthus species, (pigweeds and amaranths, AMASS), Ammannia coccinea Rottb. (redstem, AMMCO), Commelina benghalensis L. (Benghal dayflower, COMBE), Eclipta alba (L.) Hassk. (American false daisy, ECLAL), Heteranthera limosa (SW.) Willd./Vahl (ducksalad, HETL1), Heteranthera reniformis R. & P. (roundleaf mudplantain, HETRE), Ipomoea species (morningglories, IPOSS), Ipornoea hederacea (L.) Jacq.
(ivyleaf morningglory, IPOHE), Lindernia dubia (L.) Pennell (low false pimpernel, LIDDU), Ludwigia species (LUDSS), Ludwigia linifolia Poir. (southeastern primrose-willow, LUDL1), Ludwigia octovalvis (Jacq.) Raven (longfruited primrose-willow, LUDOC), Monochoria korsakowii Regel & Maack (monochoria, MOOKA), Monochoria vaginalis (Burm. F.) C.
Presl ex Kuhth, (monochoria, MOO VA), Murdannia nudiflora (L.) Brenan (doveweed, MUDNU), Polygonum pensylvanicum L., (Pennsylvania smartweed, POLPY). Polygonum persicaria L. (ladysthumb, POLPE), Polygonum hydropz:peroides Michx. (POLHP, mild smartweed), Rotala id/ca (Willd.) Koehne (Indian toothcup, ROTIN), Sagittaria species, (arrowhead, SAGSS), Sesbania exaltata (Raf.) Cory/Rydb. Ex Hill (hemp sesbania, SEBEX), or Sphenoclea zeylanica Gaertn. (gooseweed, SPDZE).
In some embodiments, the methods provided herein are utilized to control undesirable vegetation in cereals. In certain embodiments, the undesirable vegetation is Alopecurus myosuroides Huds. (blackgrass, ALOMY), Apera spica-venti (L.) Beauv.
(windgrass, APESV), Avena fatua L. (wild oat, AVEFA). Bromus tectorum L. (downy brome, BROTE), Lolium multiflorumLarn. (Italian ryegrass, LOLMIJ), Phalaris minor Retz.
(littleseed canarygrass, PHAMI), Poa annua L. (annual bluegrass, POANN), Setaria pumila (Poir.) Roemer & J.A. Schultes (yellow foxtail, SULU), Setaria viridis (L.) Beauv.
(green foxtail, SETVI), Amaranthus retroflexus L. (redroot pig-weed, AMARE), Brass/ca species (BRSSS), Chenopodium album L. (common lambsquarters, CHEAL), Cirsium arvense (L.) Scop.
(Canada thistle, CIRAR), Gal/urn aparine L. (catchweed bedstraw, GALAP).
Kochia scoparia (L.) Schrad. (kochia, KCHSC), Lanham purpureum L. (purple deadnettle , LAMPU), Matricaria recutita L. (wild chamomile, MATCH), Matricaria matricarioides (Less.) Porter (pineappleweed, MA.TMT), .Papaver rhoeas L. (common poppy, PAPRH), Polygonum convolvulus L. (wild buckwheat, POLCO), Salsola tragus L. (Russian thistle, SASKR), Sinapis species (SINSS), Sinapis arvensis L. (wild mustard, SINAR) Stellaria media (L.) Vill. (common chickweed, STEME), Veronica persica Poir. (Persian speedwell, VERPE), Viola arvensis Murr. (field violet, VIOAR), or Viola tricolor L. (wild violet, VIOTR).

SUBSTITUTE SHEET (RULE 26) in some embodiments, the methods provided herein are utilized to control undesirable vegetation in range and pasture, &Howland, 1VM and ROW. In certain embodiments, the undesirable vegetation is Ambrosia artemisiffolia L. (common ragweed, AMBEL), Cassia obtustfolia (sickle pod, CASOB), Centaurea maculosa auct. non Lam. (spotted Imapweed, CENMA), Cirsium arvense (L.) Scop. (Canada thistle, CIRAR), Con volvulus arvensis L.
(field bindweed, CONAR), Dauco carota L. (wild carrot, DAUCA), Euphorbia esula L.
(leafy spurge, EPHES). Lactuca serriola L./Tom. (prickly lettuce, LACSE), Plantago lanceolata L. (buckhom plantain, PLALA), Rumex obtusgblius L. (broadleaf dock, RUMOB), Sida .spinosa L. (prickly sida, SIDSP), Sinapis arvensis L. (wild mustard, S1NAR), Sonchus arvensis L. (perennial sowthistle, SONAR), Solidago species (goldenrod, SOOSS), Taraxacum qfficinak G.H. Weber ex Wiggers (dandelion, TAROF), Trifolium repens L.
(white clover, TRFRE), or Urtica dioica L. (common nettle, URTD1).
In some embodiments, the methods provided herein are utilized to control undesirable vegetation found in row crops, tree and vine crops and perennial crops. In certain embodiments, the undesirable vegetation is Alopecurus myosuroides Huds.
(blackgrass, ALOMY), Avena fatua L. (wild oat, AVEFA), Brachiaria decumbens Stapf. or Urochloa decurnbens (Stapf) R.D. Webster (Surinam grass, BRADC), Brachiaria brizantha (Hoch.st. ex A. Rich.) Stapf. or Urochloa brizantha (Hochst. ex A. Rich.) R.D. (beard grass, BRABR), Brachiaria platyphylla (Groseb.) Nash or Urochloa platyphylla (Nash) R.D.
Webster (broadleaf signalgrass, I3RAPP), .Brachiaria plantaginea (Link) Hitchc. or Urochloa plantaginea (Link) R..D. Webster (alexandergrass, BRAPL), Cenchrus echinatus L. (southern sandbur, CENEC). Digitaria horizontalis Willd. (Jamaican crabgrass, DIGHO), Digitaria insularis (L.) Mez ex Ekman (sourgrass, IRON), Digitaria sanguinalis (L.) Scop. (large crabgrass, DIGSA), Echinochloa crus-galli (L.) P. Beauv. (bamyardgrass, ECHCG), Echinochloa colonum (L.) Link (junglerice, ECHCO), Eleusine id/ca (L.) Gaertn.
(goosegrass, ELEIN), Lollum multiflorum Lam. (Italian ryegrass, LOLMU), Panicum dichotomiflorum Michx. (WI panicum, PANDD, .Panicum miliaceum L. (wild-proso millet, PANMI), Setaria faberi Herrn (giant foxtail, SETFA), Setaria viridis (L.) Beauv. (green foxtail, SETVO, Sorghum halepense (L.) Pers. (Johnsongrass, SORHA), Sorghum bicolor (L.) Moench ssp. Arundinaceum (shattercane, SORVU), Cyperus esculentus L.
(yellow nutsedge, CYPES), C:yperus rotundus L. (purple nutsedge, CYPRO), Abut/ion theophrasti Medik. (velvetleaf, ABUTH), Amaranthus species (pigweeds and amaranths, AMASS), Ambrosia artemisiifolia L. (common ragweed, AMBEL), Ambrosia psilostachya DC.
(western ragweed, AMBPS), Ambrosia trifida L. (giant ragweed, AMBTR), Anoda cristata SUBSTITUTE SHEET (RULE 26) (L.) Schlecht. (spurred anoda, ANVCR), Asclepias syriaca L. (common milkweed, ASCSY), Bidens pilosa L. (hairy beggarticks, BIDPI), Borreria species (BOISS), Borreria alata (Aubl.) DC. or Spermacoce alata Aubl. (broadleaf buftonweed, BOILF), Spermacose la4folia (broadleaved button weed, BOILF), Chenopodium album L. (common lambsquarters, CHEAL), Cirsium arvense (L.) Scop. (Canada thistle, CIRAR), Commelina benghalensis L.
(tropical spiderwort, COMBE), .Datura stramonium L. (jimsonweed, DATST), Daucus carota L. (wild carrot, DAUCA). Euphorbia heterophylla L. (wild poinsettia, EPHHL), Euphorbia hirta L. or Chamaesyce hirta (L.) Millsp. (garden spurge, EPHHI), Euphorbia dentata Michx. (toothed spurge, EPIIDE), Erigeron bonariensis L. or Conyza bonariensis (L.) Cronq. (hairy fleabane, ERIBO), Erigeron canadensis L. or Conyza canadensis (L.) Cronq. (Canadian fleabane, ERICA), Con.vza sumatrensis (Retz.) E. H. Walker (tall fleabane, ERIFL), Helianthus annuus L. (common sunflower, HELAN), facquemontia tamnifolia (L.) Griseb. (smallflower morningglory, IAQTA), Ipomoea hederacea (L.) Jacq.
(ivyleaf momingglory, IPOHE), Ipomoea lacunosa L. (white momingglory, IPOLA), Lactuca serriola L./Tom. (prickly lettuce, LACSE), Portulaca oleracea L. (common purslane, POROL), Richardia species (pusley, RCIISS), Sida species (sida, SIDSS), Sida spinosa L.
(prickly sida, SIDSP), Sinapis arvensis L. (wild mustard, SINAR), Solanum ptychanthum Dunal (eastern black nightshade, SOLPT), Tridax procumbens L. (coat buttons, TRQPR), Tridax procumbens L. (coat buttons, TRQPR), or Xanthium strumarium L. (common cocklebur, XANST).
In some embodiments, the methods provided herein are utilized to control undesirable vegetation in turf. In certain embodiments, the undesirable vegetation is Bells perennis L.
(English daisy, BELPE), Cypenes esculentus L. (yellow nutsedge, CYPES), Cypenis species (CYPSS), Digitaria sanguinalis (L.) Scop. (large crabgrass, DIGSA), Diodia virginiana L.
(Virginia buftonweed, DIQVI), Euphorbia species (spurge, EPHSS), Glechoma hederacea L.
(ground ivy, GLEHE), Hydrocotyle umbellata L. (dollarweed, HYDUM), Kyllinga species (kyllinga, KYLSS), Lamium amplexicauk L. (henbit, LAMAM), Murdannia nudiflora (L.) Brenan (doveweed, MUDNU), Oxalis species (woodsorrel, OXASS), Plantago major L.
(broadleaf plantain, PLAMA), Plantago lanceolata L. (buckhortharrowleaf plantain, PLALA), Phyllanthu,s urinaria L. (chamberbitter, PYLTE), .Rumex obtusifollus L. (broadleaf dock, RUMOB), Stachys floridana Shuttlew. (Florida betony, STAFL), Stellaria media (L.) Vill. (common chickweed, STEME), Taraxacum officinale G.H. Weber ex Wiggers (dandelion, TAROF), Trifolium repens L. (white clover, TRFRE), or Viola species (wild violet, VIOSS).

SUBSTITUTE SHEET (RULE 26) In some embodiments, the compositions and methods provided herein are utilized to control undesirable vegetation consisting of grass, broadleaf and sedge weeds.
In certain embodiments, the compositions and methods provided herein are utilized to control undesirable vegetation including Avena, Brachiaria, Cyperus, Digitaria, Echinochloa, Fimbristylis, Ipontoea, Ischaemum, Leptochloa, Lolium, Schoenoplectus and Sesbania.
In some embodiments, the combination of compound (I) or agriculturally acceptable ester or salt thereof and ACCase inhibitors or agriculturally acceptable salt or ester thereof is used to control Avena fatua L.(wild oat, AVEFA), Brachiaria platyphylla (Griseb.) Nash (broadleaf signalgrass, BRAPP), Ciperus diffbrmis L. (smallflower umbrella sedge, CYPDI), cypera.s esculentus L. (yellow nutsedge, CYPES), cvperus iria L. (rice flatsedge, CYPIR), Cyperus rotundus L. (purple nutsedge, CYPRO), Digitaria sanguinalis (L.) Scop.
(large crabgrass, DIGSA), Echinochka crus-galli (L.) Beauv. (barnyardgrass, ECHCG), Echinochloa wlona (L.) Link (junglerice, ECHCO), Fimbristylis miliacea (L.) Vahl (globe fringerush, FIMMI). Ipomoea hederacea Jacq. (ivyleaf momingglory, IPOHE), Ischaemum rugosunt Salisb. (saramollagrass, ISCRU), Leptochloa chinensis (L.) Nees (Chinese sprangletop, LEFCII), Lolium multiflorum Lam. (Italian ryegrass, LOLMU), Schoenoplectus juncoides (Roxb.) Palla (Japanese bulrush, SCPJU), Schoenoplectus maritimus (L.) Lye (sea clubrush, SCPMA), Schoenoplectus mucronatus (ricefield bulrush, SCPMU) and Sesbania exaltata (hemp sesbania , SEBEX).
The compounds of formula I or agriculturally acceptable salt or ester thereof may be used to control herbicide resistant or tolerant weeds. The methods employing the combination of a compound of formula I or agriculturally acceptable salt or ester thereof and the compositions described herein may also be employed to control herbicide resistant or tolerant weeds. Exemplary resistant or tolerant weeds include, but are not limited to, biotypes resistant or tolerant to acetolactate synthase (ALS) or acetohydroxy acid synthase (AHAS) inhibitors, (e.g., imidazolinones, sulfonylureas, pyrimidinylthiobenzoates, triazolopyrimidines, sulfonylaminocarbonyltriazolinones), photosystem H
inhibitors (e.g., phenylcarbamates, pyridazinories, triazines, triazinon.es, uracils, amides, ureas, benzothiadiazinones, nitriles, phenylpyridazines), acetyl CoA carboxylase (ACCase) inhibitors (e.g., aryloxyphenoxypropionates, cyclohexanediones, phenylpyra2olines), synthetic auxins, (e.g., benzoic acids, phenoxycarboxylic acids, pyridine carboxylic acids, quinoline carboxylic acids), auxin transport inhibitors (e.g., phthalamates, semicarbazones), photosystem I inhibitors, (e.g., bipyridyliums), 5-enolpyruvylshikimate-3-phosphate (EPSP) synthase inhibitors, (e.g., glyphosate), glutamine synthetase inhibitors (e.g., glufosinate, SUBSTITUTE SHEET (RULE 26) bialafos), microtubule assembly inhibitors, (e.g., benzamides, benzoic acids, dinitroanilines, phosphoramidates, pyridines), mitosis inhibitors (e.g., carbamates), very long chain fatty acid (VIEFA) inhibitors (e.g., acetamides, chloroacetamides, oxyacetamides, tetrazolinones), fatty acid and lipid synthesis inhibitors, (e.g., phosphorodithioates, thiocarbamates, benzofuranes, chlorocarbonic acids), protoporphyrinogen oxidase (PPO) inhibitors (e.g., diphenylethers, N-phenylphthalimides, oxadiazoles, oxazolidinediones, phenylpyrazoles, pyrimidindiones, thiadiazoles, triazolinones), carotenoid biosynthesis inhibitorsõ phytoene desaturase (PDS) inhibitors (e.g., amides, anilidex, fitranones, phenoxybutan-amides, pyridiazinones, pyridines), 4-hydroxyphenyl-pyruvate-dioxygenase (EIPPD) inhibitors, (e.g., callistemones, isoxazoles, pyrazoles, triketones), cellulose biosynthesis inhibitors (e.g., nitriles, benzamides, quinclorac, triazolocatboxamides), mitosis inhibitors, cellulose biosynthesis inhibitors, herbicides with multiple modes-of-action such as quinclorac, and unclassified herbicides such as arylaminopropionic acids, difenzoquat, endothall, and organoarsenicals. Exemplary resistant or tolerant weeds include, but are not limited to, biotypes with resistance or tolerance to multiple herbicides, biotypes with resistance or tolerance to multiple chemical classes, biotypes with resistance or tolerance to multiple herbicide modes-of-action and biotypes with multiple resistance or tolerance mechanisms (e.g., target site resistance or metabolic resistance).
In some embodiments, an agriculturally acceptable ester or salt of compound (I) is employed. In certain embodiments, an agriculturally acceptable ester is employed. In certain embodiments, the ester is a C1..4 alkyl ester. In certain embodiments, the ester is an n-butyl ester. In certain embodiments, the ester is a benzyl ester. In certain embodiments, compound (I), which is a carboxylic acid, is employed.
In certain embodiments of the compositions and methods described herein, the compound of formula (I) or salt or ester thereof is used in combination with clethodim or salt or ester thereof. With respect to the compositions, in some embodiments, the weight ratio of the compound of formula (I) or salt or ester thereof to clethodim or salt or ester thereof is within the range of from about 1:140 to about 9:1. In certain embodiments, the weight ratio of the compound of formula (I) or salt or ester thereof to clethodim or salt or ester thereof is within the range of from about 1:48 to about 3:1. In certain embodiments, the compositions provided herein comprise the compound of formula (I) or its benzyl or n-butyl ester and clethodim.. With respect to the methods, in certain embodiments, the methods comprise contacting the undesirable vegetation or locus thereof or applying to the soil or water to SUBSTITUTE SHEET (RULE 26) prevent the emergence or growth of vegetation a composition described herein.
In some embodiments, the composition is applied at an application rate of from about 20 grams active ingedient per hectare (gailha) to about 580 gailha based on the total amount of active ingredients in the composition. In certain embodiments, the composition is applied at an application rate of from about 20 grams active ingredient per hectare (gai/ha) to about 260 gailha based on the total amount of active ingredients in the composition. In some embodiments, the methods comprise contacting the undesirable vegetation or locus thereof or applying to the soil or water to prevent the emergence or growth of vegetation with a compound of formula (I) or salt or ester thereof and clethodim or salt thereof, e.g., sequentially or simultaneously. In some embodiments, the clethodim or salt thereof is applied at a rate from about 17.5 gai/ha to about 280 gailha and the compound of formula (1) of salt or ester thereof is applied at a rate from about 2 gae/ha to about 300 gae/ha. In some embodiments, the clethodim or salt thereof is applied at a rate from about 70 gai/ha to about 280 gai/ha and the compound of formula (1) of salt or ester thereof is applied at a rate from about 8 gaetha to about 32 gaelha. In certain embodiments, the methods utilize the compound of formula (I), or its benzyl or n-butyl ester and clethodim %r the control of BRAPP, DIGSA, CYPES and SCPJU.
In certain embodiments of the compositions and methods described herein, the compound of formula (I) or salt or ester thereof is used in combination with clodinafop-propargyl or salt, carboxylate salt, carboxylic acid, or ester thereof. With regard to the compositions, in some embodiments, the weight ratio of the compotmd of formula (I) or salt or ester thereof to clodinafop-propargyl or salt, carboxylate salt, carboxylic acid, or ester thereof is within the range of from about 1:40 to about 60:1. In certain embodiments, the weight ratio of the compound of formula (I) or salt or ester thereof to clodinafop-propargyl or salt, carboxylate salt, carboxylic acid, or ester thereof is within the range of from 1:36 to about 10:1. In certain embodiments, the weight ratio of the compound of formula (1) or salt or ester thereof to clodinafop-propargyl or salt, carboxylate salt, carboxylic acid, or ester thereof is within the range of from 1:6 to about 1:1.5. In certain embodiments, the compositions provided herein comprise the compound of formula (0 or its benzyl or n-butyl ester and clodinafop-propargyl. With respect to the methods, in certain embodiments, the methods comprise contacting the undesirable vegetation or locus thereof or applying to the soil or water to prevent the emergence or growth of vegetation a composition described herein. In some embodiments, the composition is applied at an application rate of from about 7 grams active ingredient per hectare (gai/ha) to about 380 gailha based on the total amount SUBSTITUTE SHEET (RULE 26) of active ingredients in the composition. In certain embodiments, the composition is applied at an application rate of from about 20 grams active ingredient per hectare (gai/ha) to about 40 gai/ha based on the total amount of active ingredients in the composition.
In some embodiments, the methods comprise contacting the undesirable vegetation or locus thereof or applying to the soil or water to prevent the emergence or growth of vegetation with a compound of formula (I) or salt or ester thereof and clodinafop-propargyl or salt, carboxylate salt, carboxylic acid, or ester thereof, e.g., sequentially or simultaneously.
In some embodiments, the clodinafop-propargyl or salt, carboxylate salt, carboxylic acid, or ester thereof is applied at a rate from about 5 gai/ha to about 80 gai/ha and the compound of formula (I) of salt or ester thereof is applied at a rate from about 2 gae/ha to about 300 gae/ha.
In some embodiments, the clodinafop-propargyl or salt, carboxylate salt, carboxylic acid, or ester thereof is applied at a rate from about 15 gai/ha to about 30 gai/ha and the compound of formula (I) of salt or ester thereof is applied at a rate from about 5 gaelha to about 10 gaeiha.
In one embodiment, the methods utilize the benzyl ester of the compound of formula (I) and clodinafop-propargl are used to control LOLMU, KCHSC, PHAMI, APESV and ALOMY.
In certain embodiments of the compositions and methods described herein, the compound of formula (I) or salt or ester thereof is used in combination with cyhalofop-R-butyl or carboxylic acid, carboxylate salt, or ester thereof. With respect to the compositions, in some embodiments, the weight ratio of the compound of formula (I) or salt or ester thereof to cyhalofop-R-butyl carboxylic acid, carboxylate salt, or ester thereof is within the range of from about 1:155 to about 6:1. In certain embodiments, the weight ratio of the compound of formula (I) or salt or ester thereof to cyhalofop-R-butyl or carboxylic acid, carboxylate salt, or ester thereof is within the range of from 1:32 to about 1:4. In certain embodiments, the weight ratio of the compound of formula (I) or salt or ester thereof to cyhalofop-R-butyl or carboxylic acid, carboxylate salt, or ester thereof is within the range of from about 1:42 to about 10:1. In certain embodiments, the weight ratio of the compound of formula (I) or salt or ester thereof to cyhalotbp-R-butyl or carboxylic acid, carboxylate salt, or ester thereof is within the range of from about 1:21 to about 5:1. In certain embodiments, the compositions provided herein comprise the compound of formula (I) or its benzyl ester and cyhalofop-R-butyl. In one embodiment, the composition comprises the compound of formula (I) and cyhalofop-R-butyl, wherein the weight ratio of the compound of formula (I) to cyhalofop-R-butyl is about 1:20.6 to about 1:2.5. in one embodiment, the composition comprises the benzyl ester of the compound of formula (I) and cyhalofop-R-butyl, wherein the weight ratio of the benzyl ester of the compound of formula (I) to cyhalofop-R-butyl is about 1:23 to SUBSTITUTE SHEET (RULE 26) about 5:1. With respect to the methods, in certain embodiments, the methods comprise contacting the undesirable vegetation or locus thereof or applying to the soil or water to prevent the emergence or growth of vegetation a composition described herein.
In some embodiments, the composition is applied at an application rate of from about 52 grams active ingredient per hectare (gai/ha) to about 610 gaitha based on the total amount of active ingredients in the composition. In certain embodiments, the composition is applied at an application rate of from about 99 grams active ingredient per hectare (gal/ha) to about 320 gai/ha based on the total amount of active ingredients in the composition. In some embodiments, the methods comprise contacting the undesirable vegetation or locus thereof or applying to the soil or water to prevent the emergence or growth of vegetation with a compound of formula (I) or salt or ester thereof and cyhalofop-R-butyl or carboxylic acid, carboxylate salt, or ester thereof, e.g., sequentially or simultaneously. In some embodiments, the cyhalofop-R-butyl or salt or ester thereof is applied at a rate from about 50 gai/ha to about 310 gai/ha and the compound of formula a) of salt or ester thereof is applied at a rate from about 2 gae/ha to about 300 gae/ha. In some embodiments, the cyhalofop-R-butyl or carboxylic acid, carboxylate salt, or ester thereof is applied at a rate from about 45 gai/ha to about 600 gai/ha and the compound of formula (I) of salt or ester thereof is applied at a rate from about 4 g acid equivalent per hectare (gae/ha) to about 85 gae/ha. In some embodiments, the cyhalofop-R-butyl or carboxylic acid, carboxylate salt, or ester thereof is applied at a rate from about 90 gal/ha to about 300 gal/ha and the compound of formula (t) of salt or ester thereof is applied at a rate from about 8 g acid equivalent per hectare (gae/ha) to about 42 gae/ha. In certain embodiments, the methods utilize the compound of formula (1), or its benzyl ester and cyhalofop-R-butyl. In one embodiment, the methods utilize the compound of formula (I) and cyhalofop-R-butyl, wherein the compound of formula (I) is applied at a rate of from about 8.75 g acid equivalent per hectare (gae/ha) to about 42.4 gae/ha, and cyhalofop-R-butyl is applied at a rate of about 90 gai/ha to about 280 gal/ha. In one embodiment, the methods utilize the benzyl ester of the compound of formula (I) and cyhalofop-R-butyl, wherein the benzyl ester of the compound of formula (I) is applied at a rate of from about 8.75 g acid equivalent per hectare (gaelha) to about 35 gae/ha, and cyhalofop-R-butyl is applied at a rate of about 90 gal/ha to about 300 gai/ha.
In certain embodiments, the methods and compositions utiMng the compound of formula (I) or salt or ester thereof in combination with cyhalofop-R-butyl or carboxylic acid, carboxylate salt, or ester thereof are used to control ISCRU, 1POHE, ECHOR, SCPSU, LEFCH, SCPMA, CYPIR, FIMMI, SEBEX, CYPDI, ECIICG, ECIISS, or SCPMU.

SUBSTITUTE SHEET (RULE 26) In certain embodiments of the compositions and methods described herein, the compound of formula (I) or salt or ester thereof is used in combination with diclothp-methyl or carboxylic acid, carboxylate salt, or ester thereof. With regard to the compositions, in some embodiments, the weight ratio of the compound of formula (I) or salt or ester thereof to diclofop-methyl or carboxylic acid, carboxylate salt, or ester thereof is within the range of from about 1:560 to about 5:1. In certain embodiments, the weight ratio of the compound of formula ( 1-) or salt or ester thereof to diclofop-methyl or carboxylic acid, carboxylate salt, or ester thereof is within the range of from 1:255 to about 1:1. In certain embodiments, the weight ratio of the compound of thrmula (I) or salt or ester thereof to diclofop-methyl or carboxylic acid, carboxylate salt, or ester thereof is within the range of from 1:140 to about 1:9 .1n certain embodiments, the compositions provided herein comprise the compound of formula (I) or its benzyl or n-butyl ester and diclofop-methyl. With respect to the methods, in certain embodiments, the methods comprise contacting the undesirable vegetation or locus thereof or applying to the soil or water to prevent the emergence or gowth of vegetation a composition described herein. In some embodiments, the composition is applied at an application rate of from about 72 grams active ingredient per hectare (gaiiha) to about 1,420 gailha based on the total amount of active ingredients in the composition. In certain embodiments, the composition is applied at an application rate of from about 73 grams active ingredient per hectare (gai/ha) to about 610 gal/ha based on the total amount of active ingredients in the composition. In some embodiments, the methods comprise contacting the undesirable vegetation or locus thereof or applying to the soil or water to prevent the emergence or growth of vegetation with a compound of formula (I) or salt or ester thereof and diclofop-methyl or salt or ester thereof, e.g., sequentially or simultaneously. In some embodiments, the diclofop-methyl or salt or ester thereof is applied at a rate from about 70 gai/ha to about 1,120 gai/ha and the compound of formula (I) of salt or ester thereof is applied at a rate from about 2 gae/ha to about 300 gae/ha. In certain embodiments, the methods utilize the compound of thrmula (I), or its benzyl or n-butyl ester and diclofop-methyl are used to control APESV, CY PIR, KCHSC and PHAMI.
In certain embodiments of the compositions and methods described herein, the compound of formula (I) or salt or ester thereof is used in combination with fenoxaprop-P-ethyl or carboxylic acid or carboxylate salt thereof or other ester, and fenoxaprop-P-ethyl can be applied alone or in combination with the safeners isoxadifen-ethyl or mefenpyr-diethyl.
With regard to the compositions, in some embodiments, the weight ratio of the compound of thrmula (I) or salt or ester thereof to fenoxaprop-P-ethyl or carboxylic acid or carboxylate salt SUBSTITUTE SHEET (RULE 26) thereof or other ester is within the range of from about 1:170 to about 30:1.
In certain embodiments, the weight ratio of the compound of formula (I) or salt or ester thereof to fenoxaprop-P-ethyl or carboxylic acid or carboxylate salt thereof or other ester is within the range of from 1:16 to about 1.5:1. In certain embodiments, the weight ratio of the compound of formula (I) or salt or ester thereof to fenoxaprop-P-ethyl or carboxylic acid or carboxylate salt thereof or other ester is within the range of from 1:16 to about 3:1. In certain embodiments, the weight ratio of the compound of formula (I) or salt or ester thereof to fenoxaprop-P-ethyl or carboxylic acid or carboxylate salt thereof or other ester is within the range of from about 1:32 to about 4:1. In certain embodiments, the weight ratio of the compound of formula (I) or salt or ester thereof to fenoxaprop-P-ethyl or carboxylic acid or carboxylate salt thereof or other ester is within the range of from about 1:16 to about 2:1. In certain embodiments, the compositions provided herein comprise the compound of formula (I) or its benzyl ester and fenoxaprop-P-ethyl. In one embodiment, the composition comprises the compound of formula (I) and fenoxaprop-P-ethyl, wherein the weight ratio of the compound of formula (I) to fenoxaprop-P-ethyl is about 1:14 to about 2:1.
In one embodiment, the composition comprises the benzyl ester of the compound of formula (I) and fenoxaprop-P-ethyl, wherein the weight ratio of the benzyl ester of the compound of formula (I) to fenoxaprop-P-ethyl is about 1:16 to about 1:1. With respect to the methods, in certain embodiments, the methods comprise contacting the undesirable vegetation or locus thereof or applying to the soil or water to prevent the emergence or growth of vegetation a composition described herein. In some embodiments, the composition is applied at an application rate of from about 13 grams active ingredient per hectare (gal/ha) to about 44.0 gal/ha based on the total amount of active ingredients in the composition. In certain embodiments, the composition is applied at an application rate of from about 15 grams active ingredient per hectare (gal/ha) to about 90 gal/ha based on the total amount of active ingredients in the composition. In some embodiments, the methods comprise contacting the undesirable vegetation or locus thereof or applying to the soil or water to prevent the emergence or growth of vegetation with a compound of formula 0.) or salt or ester thereof and fenoxaprop-P-ethyl or salt or ester thereof, e.g., sequentially or simultaneously. In some embodiments, the fenoxaprop-P-ethyl or carboxylic acid or carboxylate salt thereof or other ester is applied at a rate from about 11 gal/ha to about 140 gal/ha and the compound of formula (I) of salt or ester thereof is applied at a rate from about 2 gae/ha to about 300 gae/ha. In some embodiments, the fenoxaprop-P-ethyl or carboxylic acid or carboxylate salt thereof or other ester is applied at a rate from about 5 gai/ha to about 300 gai/ha and the compound of formula SUBSTITUTE SHEET (RULE 26) (I) of salt or ester thereof is applied at a rate from about 2 g acid equivalent per hectare (gae/ha) to about 90 gae/ha. In some embodiments, the fenoxaprop-P-ethyl or carboxylic acid or carboxylate salt thereof or other ester is applied at a rate from about 11.5 gal/ha to about 140 gai/ha and the compound of formula (1) of salt or ester thereof is applied at a rate from about 4.38 g acid equivalent per hectare (gull* to about 42.4 gae/ha. In certain embodiments, the methods utilize the compound of formula (I), or its benzyl ester and fenoxaprop-P-ethyl. In one embodiment, the methods utilize the compound of formula (I) and fenoxaprop-P-ethyl, wherein the compound of formula (I) is applied at a rate of from about 4.38 g acid equivalent per hectare (gae/ha) to about 42.4 gae/ha, and fenoxaprop-P-ethyl is applied at a rate of about 11.5 gailha to about 140 gai/ha. In one embodiment, the methods utilize the benzyl ester of the compound of formula (I) and fenoxaprop-P-ethyl, wherein the benzyl ester of the compound of formula (I) is applied at a rate of from about 4.38 g acid equivalent per hectare (gae/ha) to about 35 gae/ha, and fenoxaprop-P-ethyl is applied at a rate of about 17.5 gal/ha to about 70 gal/ha. In certain embodiments, the methods and compositions utilizing the compound of formula (I) or salt or ester thereof in combination with fenoxaprop-P-ethyl or carboxylic acid or carboxylate salt thereof or other ester are used to control CYPIR, ECHOR, FIMMI, SCPJU, CYPES, KCHSC, PHAMI and APESV.
In certain embodiments of the compositions and methods described herein, the compound of formula (I) or salt or ester thereof is used in combination with fluazifop-P-butyl or carboxylic acid or carboxylate salt thereof or other ester. With regard to the compositions, in some embodiments, the weight ratio of the compound of formula (I) or salt or ester thereof to fluazifop-P-butyl or carboxylic acid or carboxylate salt thereof or other ester is within the range of from about 1:210 to about 3:1. In certain embodiments, the weight ratio of the compound of formula (I) or salt or ester thereof to fluazifop-P-butyl or carboxylic acid or carboxylate salt thereof or other ester is within the range of from 1:41 to about 2.5:1. In certain embodiments, the weight ratio of the compound of formula (I) or salt or ester thereof to fluazifop-P-butyl or carboxylic acid or carboxylate salt thereof or other ester is within the range of from 1:41 to about 1:1. In certain embodiments, the weight ratio of the compound of formula (I) or salt or ester thereof to fluazifop-P-butyl or salt or ester thereof is within the range of from about 1:80 to about 1:1. In certain embodiments, the weight ratio of the compound of formula 0.) or salt or ester thereof to fluazifop-P-butyl or salt or ester thereof is within the range of from about 1:36 to about 1:2.5. In certain embodiments, the compositions provided herein comprise the compound of formula (I) or its benzyl ester and fluazifop-P-butyl. In one embodiment, the composition comprises the compound of formula (I) and RECTIFIED (RULE 91) - ISA/US

fluazifop-P-butyl, wherein the weight ratio of the compound of formula (I) to fluazifop-P-butyl is about 1:36 to about 1:2.5. In one embodiment, the composition comprises the benzyl ester of the compound of formula (I) and fluazifop-P-butyl, wherein the weight ratio of the benzyl ester of the compound of formula (I) to fluazifop-P-butyl is about 1:36 to about 1:5.1.
With respect to the methods, in certain embodiments, the methods comprise contacting the undesirable vegetation or locus thereof or applying to the soil or water to prevent the emergence or growth of vegetation a composition described herein. In some embodiments, the composition is applied at an application rate of from about 47 grams active ingredient per hectare (gaiiha) to about 720 gaiiha based on the total amount of active ingredients in the composition. In certain embodiments, the composition is applied at an application rate of from about 50 grams active ingredient per hectare (gai/ha) to about 200 gai/ha based on the total amount of active ingredients in the composition. In some embodiments, the methods comprise contacting the undesirable vegetation or locus thereof or applying to the soil or water to prevent the emergence or growth of vegetation with a compound of formula (I) or salt or ester thereof and fluazifop-P-butyl or salt or ester thereof, e.g., sequentially or simultaneously. In some embodiments, the fluazifop-P-butyl or carboxylic acid or carboxylate salt thereof or other ester is applied at a rate from about 45 gae/ha to about 420 gae/ha and the compound of formula (1) of salt or ester thereof is applied at a rate from about 2 gae/ha to about 300 gae/ha. In some embodiments, the fluazifop-P-butyl or carboxylic acid or carboxylate salt thereof or other ester is applied at a rate from about 20 gai/ha to about 400 gal/ha and the compound of formula (I) of salt or ester thereof is applied at a rate from about 2 g acid equivalent per hectare (gae/ha) to about 70 gae/ha. In some embodiments, the fluazifbp-P-butyl or carboxylic acid or carboxylate salt thereof or other ester is applied at a rate from about 45 gailha to about 180 gai/ha and the compound of formula (I) of salt or ester thereof is applied at a rate from about 4.38 g acid equivalent per hectare (gae/ha) to about 35 gae/ha. In certain embodiments, the methods utilize the compound of formula (I), or its benzyl ester and fluazifop-P-butyl. In one embodiment, the methods utilize the compound of formula (I) and fluazifop-P-butyl, wherein the compound of formula (I) is applied at a rate of from about 4.38g acid equivalent per hectare (gaelha) to about 35 gae/ha, and fluazifop-P-butyl is applied at a rate of about 45 gaiiha to about 180 gai/ha. In one embodiment, the methods utilize the benzyl ester of the compound of formula (I) and fluazifop-P-butyl, wherein the benzyl ester of the compound of formula (I) is applied at a rate of from about 4.38 g acid equivalent per hectare (gae/ha) to about 8.75 gaelha, and fluazifop-P-butyl is applied at a rate of about 45 gai/ha to about 180 gal/ha. In certain embodiments, the methods SUBSTITUTE SHEET (RULE 26) and compositions utilizing the compound of formula (I) or salt or ester thereof in combination with fluazifop-P-butyl or carboxylic acid or carboxylate salt thereof or other ester are used to control IPOHE, ECHOR, or CYPRO.
In certain embodiments of the compositions and methods described herein, the compound of formula (I) or salt or ester thereof is used in combination with haloxyfop-R-methyl or carboxylic acid or carboxylate salt thereof or other ester. With regard to the compositions, in some embodiments, the weight ratio of the compound of formula (I) or salt or ester thereof to haloxyfop-R-methyl or carboxylic acid or carboxylate salt thereof or other ester is within the range of from about 1:45 to about 10:1. In certain embodiments, the weight ratio of the compound of formula (I) or salt or ester thereof to haloxyfop-R-methyl or carboxylic acid or carboxylate salt thereof or other ester is within the range of from 1:6 to about 2.5:1. In certain embodiments, the weight ratio of the compound of formula (I) or salt or ester thereof to haloxyfop-R-methyl or carboxylic acid or carboxylate salt thereof or other ester is within the range of from about 1:15 to about 6:1. In certain embodiments, the weight ratio of the compound of formula (I) or salt or ester thereof to haloxyfop-R-methyl or carboxylic acid or carboxylate salt thereof or other ester is within the range of from about 1:7 to about 2.6:1. In certain embodiments, the compositions provided herein comprise the compound of formula (I) or its benzyl ester and haloxyfop-R-methyl. In one embodiment, the composition comprises the compound of formula (I) and haloxyfop-R-methyl, wherein the weight ratio of the compound of formula (D to haloxyfop-R-methyl is about 1:6.2 to about 2.6:1. In one embodiment, the composition comprises the benzyl ester of the compound of formula (I) and haloxyfop-R-methyl, wherein the weight ratio of the benzyl ester of the compound of formula (I) to haloxyfop-R-methyl is about 1:7 to about 1.3:1. With respect to the methods, in certain embodiments, the methods comprise contacting the undesirable vegetation or locus thereof or applying to the soil or water to prevent the emergence or growth of vegetation a composition described herein. In some embodiments, the composition is applied at an application rate of from about 32 grams active ingredient per hectare (gab/ha) to about 420 gailha based on the total amount of active ingredients in the composition. In certain embodiments, the composition is applied at an application rate of from about 10 grams active ingredient per hectare (gailha) to about 60 gailha based on the total amount of active ingredients in the composition. In some embodiments, the methods comprise contacting the undesirable vegetation or locus thereof or applying to the soil or water to prevent the emergence or growth of vegetation with a compound of formula (I) or salt or ester thereof and haloxyfop-R-methyl or carboxylic acid or carboxylate salt thereof or SUBSTITUTE SHEET (RULE 26) other ester, e.g., sequentially or simultaneously. In some embodiments, the haloxyfop-R-methyl or carboxylic acid or carboxylate salt thereof or other ester is applied at a rate from about 6.75 gaelha to about 120 gae/ha and the compound of formula (I) of salt or ester thereof is applied at a rate from about 2 gae/ha to about 300 gaetha. In some embodiments, the haloxyfop-R-methyl or carboxylic acid or carboxylate salt thereof or other ester is applied at a rate from about 3 gai/ha to about 140 gailha and the compound of formula (I) of salt or ester thereof is applied at a rate from about 2 g acid equivalent per hectare (gad*
to about 45 gae/ha. In some embodiments, the haloxyfop-R-methyl or carboxylic acid or carboxylate salt thereof or other ester is applied at a rate from about 6.75 gailha to about 70 gai/ha and the compound of formula (I) of salt or ester thereof is applied at a rate from about 4.38 g acid equivalent per hectare (gae/ha) to about 17.5 gae/ha. In certain embodiments, the methods utilize the compound of formula (I), or its benzyl or n-butyl ester and haloxyfop-R-methyl.
In one embodiment, the methods utilize the compound of formula (I) and haloxyfop-R-methyl, wherein the compound of formula (I) is applied at a rate of from about 4.38 g acid equivalent per hectare (gae/ha) to about 35 gae/ha, and haloxyfop-R-methyl is applied at a rate of about 6.75 gaiiha to about 70 gailha. In one embodiment, the methods utilize the benzyl ester of the compound of formula (I) and haloxyfop-R-methyl, wherein the benzyl ester of the compound of formula (I) is applied at a rate of from about 4.38 g acid equivalent per hectare (gae/ha) to about 17.5 gae/ha, and haloxyfop-R-methyl is applied at a rate of about 6.75 gai/ha to about 27 gai/ha. In certain embodiments, the methods and compositions utilizing the compound of formula 0.) or salt or ester thereof in combination with haloxyfop-R-methyl or carboxylic acid or carboxylate salt thereof or other ester are used to control ECHCO, IPOHE, SCP.11J, BRAPP, or CYPRO.
In certain embodiments of the compositions and methods described herein, the compound of formula (1) or salt or ester thereof is used in combination with metamifop or salt or ester thereof. With regard to the compositions, in some embodiments, the weight ratio of the compound of formula (I) or salt or ester thereof to metamifop or salt or ester thereof is within the range of from about 1:150 to about 6:1. In certain embodiments, the weight ratio of the compound of formula a) or salt or ester thereof to metamifop or salt or ester thereof is within the range of from 1:34 to about 10:1. In certain embodiments, the weight ratio of the compound of formula (I) or salt or ester thereof to metamifop or salt or ester thereof is within the range of from 1:34 to about 1:2. In certain embodiments, the weight ratio of the compound of formula (I) or salt or ester thereof to metamifop or salt or ester thereof is within the range of from about 1:60 to about 1:1. In certain embodiments, the weight ratio of the SUBSTITUTE SHEET (RULE 26) compound of formula (I) or salt or ester thereof to metamifop or salt or ester thereof is within the range of from about 1:30 to about 1:2.1. In certain embodiments, the compositions provided herein comprise the compound of formula (I) or its benzyl ester and metamifop. In one embodiment, the composition comprises the compound of formula (I) and metamifop, wherein the weight ratio of the compound of formula (I) to metamifop is about 1:30 to about 1:2.1. In one embodiment, the composition comprises the benzyl ester of the compound of formula a) and metamifop, wherein the weight ratio of the benzyl ester of the compound of formula (I) to metamifop is about 1:30 to about 1:15. With respect to the methods, in certain embodiments, the methods comprise contacting the undesirable vegetation or locus thereof or applying to the soil or water to prevent the emergence or growth of vegetation a composition described herein. In some embodiments, the composition is applied at an application rate of from about 52 grams active ingredient per hectare (pi/ha) to about 6(X) gai/ha based on the total amount of active ingredients in the composition. In certain embodiments, the composition is applied at an application rate of from about 40 grams active ingredient per hectare (gai/ha) to about 170 pi/ha based on the total amount of active ingredients in the composition. In some embodiments, the methods comprise contacting the undesirable vegetation or locus thereof or applying to the soil or water to prevent the emergence or growth of vegetation with a compound of formula 0) or salt or ester thereof and metamifop or salt or ester thereof, e.g., sequentially or simultaneously. In some embodiments, the metamifop or salt or ester thereof is applied at a rate from about 50 pi/ha to about 300 gal/ha and the compound of formula (I) of salt or ester thereof is applied at a rate from about 2 gae/ha to about 300 gaelha. In some embodiments, the metamifop or salt or ester thereof is applied at a rate from about 30 pi/ha to about 300 gailha and the compound of formula 0-) of salt or ester thereof is applied at a rate from about 2 g acid equivalent per hectare (gae/ha) to about 70 gae/ha. In some embodiments, the metamifop or salt or ester thereof is applied at a rate from about 75 gai/ha to about 150 gai/ha and the compound of formula (I) of salt or ester thereof is applied at a rate from about 4.38 g acid equivalent per hectare (gae/ha ) to about 35 gae/ha. In certain embodiments, the methods utilize the compound of formula (I), or its benzyl ester and metamifop. In one embodiment, the methods utilize the compound of formula (I) and metamifop, wherein the compound of formula (I) is applied at a rate of from about 4.38 g acid equivalent per hectare (gae/ha) to about 35 gaelha, and metamifop is applied at a rate of about 75 gai/ha to about 150 gai/ha. in one embodiment, the methods utilize the benzyl ester of the compound of formula (I) and metamifop, wherein the benzyl ester of the compound of formula (I) is applied at a rate of about 4.38 g acid equivalent per SUBSTITUTE SHEET (RULE 26) hectare (gaela), and metamifop is applied at a rate of about 75 gai/ha to about 150 gailha. In certain embodiments, the methods and compositions utilizing the compound of formula (I) or salt or ester thereof in combination with metamifop or salt or ester thereof are used to control IPOHE, ECHCG, ECHOR, IPOHE , FLMMI, SCPMA, or SMELL
In certain embodiments of the compositions and methods described herein, the compound of formula (I) or salt or ester thereof is used in combination with pinoxaden or salt or ester thereof. With regard to the compositions, in some embodiments, the weight ratio of the compound of formula (I) or salt or ester thereof to pinoxaden or salt or ester thereof is within the range of from about 1:30 to about 150:1. In certain embodiments, the weight ratio of the compound of formula (I) or salt or ester thereof to pinoxaden or salt or ester thereof is within the range of from 1:27 to about 25:1.. In certain embodiments, the weight ratio of the compound of formula (I) or salt or ester thereof to pinoxaden or salt or ester thereof is within the range of from 1:12 to about 2:1. In certain embodiments, the compositions comprise the compound of formula (I) or its benzyl or n-butyl ester and pinoxaden. With respect to the methods, in certain embodiments, the methods comprise contacting the undesirable vegetation or locus thereof or applying to the soil or water to prevent the emergence or growth of vegetation a composition described herein. In some embodiments, the composition is applied at an application rate of from about 4 grams active ingredient per hectare (gal/ha) to about 360 gal/ha based on the total amount of active ingredients in the composition. In certain embodiments, the composition is applied at an application rate of from about 8 grams active ingredient per hectare (gaiiba) to about 110 gai/ha based on the total amount of active ingredients in the composition. In some embodiments, the methods comprise contacting the undesirable vegetation or locus thereof or applying to the soil or water to prevent the emergence or growth of vegetation with a compound of formula (I) or salt or ester thereof and pinoxaden or salt thereof, e.g., sequentially or simultaneously. In some embodiments, the pinoxaden or salt or ester thereof is applied at a rate from about 2 gal/ha to about 60 gai/ha and the compound of formula (I) of salt or ester thereof is applied at a rate from about 2 gae/ha to about 300 gaelha. . In some embodiments, the pinoxaden or salt or ester thereof is applied at a rate from about 15 gailha to about 60 gal/ha and the compound of formula (I) of salt or ester thereof is applied at a rate from about 5 gae/ha to about 32 gaeiha. In certain embodiments, the methods utilize the compound of formula (I) or its benzyl or n-butyl ester and pinoxaden for the control of ECHCO, IPOHE, KCHSC, PHAMI and SCPSU.
In certain embodiments of the compositions and methods described herein, the compound of formula (D or salt or ester thereof is used in combination with profoxydim or SUBSTITUTE SHEET (RULE 26) salt or ester thereof. With regard to the compositions, in some embodiments, the weight ratio of the compound of formula (I) or salt or ester thereof to profoxydim or salt or ester thereof is within the range of from about 1:70 to about 29:1. In certain embodiments, the weight ratio of the compound of formula (I) or salt or ester thereof to profoxydim or salt or ester thereof is within the range of from 1:8 to about 2:1. In certain embodiments, the weight ratio of the compound of formula (I) or salt or ester thereof to profoxydim or salt or ester thereof is within the range of from about 1:10 to about 3:1. In certain embodiments, the weight ratio of the compound of formula (I) or salt or ester thereof to profoxydim or salt or ester thereof is within the range of from about 1:23 to about 3:1. In certain embodiments, the weight ratio of the compound of formula (I) or salt or ester thereof to profoxydim or salt or ester thereof is within the range of from about 1:5 to about 1.4:1. In certain embodiments, the compositions provided herein comprise the compound of formula (I) or its benzyl ester and profoxydim. In one embodiment, the composition comprises the compound of formula (I) and profoxydim, wherein the weight ratio of the compound of formula (1) to profoxydim is about 1:3. In one embodiment, the composition comprises the benzyl ester of the compound of formula (I) and profoxydim, wherein the weight ratio of the benzyl ester of the compound of formula (r) to profoxydim is about 1:5 to about 1.4:1. With respect to the methods, in certain embodiments, the methods comprise contacting the undesirable vegetation or locus thereof or applying to the soil or water to prevent the emergence or growth of vegetation a composition described herein. In some embodiments, the composition is applied at an application rate of from about 15 grams active ingredient per hectare (gai/ba) to about 500 gai/ha based on the total amount of active ingredients in the composition. In certain embodiments, the composition is applied at an application rate of from about 16 grams active ingredient per hectare (gai/ha) to about 50 gailha based on the total amount of active ingredients in the composition.
In some embodiments, the methods comprise contacting the undesirable vegetation or locus thereof or applying to the soil or water to prevent the emergence or growth of vegetation with a compound of formula (I) or salt or ester thereof and profoxydim or salt or ester thereof, e.g., sequentially or simultaneously. In some embodiments, the profoxydim or salt or ester thereof is applied at a rate from about 12 gai/ha to about 200 gaila and the compound of formula (I) of salt or ester thereof is applied at a rate from about 2 gae/ha to about 300 gae/ha.
In some embodiments, the profoxydim or salt or ester thereof is applied at a rate from about 4 gai/ha to about 140 gal/ha and the compound of formula (I) of salt or ester thereof is applied at a rate from about 2 g acid equivalent per hectare (gae/ha) to about 45 gaelha. In some embodiments, the profoxydim or salt or ester thereof is applied at a rate from about 12.5 SUBSTITUTE SHEET (RULE 26) gailha to about 25 gailha and the compound of formula (I) of salt or ester thereof is applied at a rate from about 4.38 g acid equivalent per hectare (gaelha) to about 17.5 gae/ha. In certain embodiments, the methods utilize the compound of formula (r), or its benzyl or n-butyl ester and profoxydim. In one embodiment, the methods utilize the compound of formula (I) and profoxydim, wherein the compound of formula (I) is applied at a rate of about 4.38 g acid equivalent per hectare (gae/ha), and profoxydim is applied at a rate of about 12.5 gai/ha. In one embodiment, the methods utilize the benzyl ester of the compound of formula (1) and profoxydim, wherein the benzyl ester of the compound of formula (I) is applied at a rate of from about 4.38 g acid equivalent per hectare (gae/ha) to about 17.5 gae/ha, and profoxydim is applied at a rate of about 12.5 gaiiha to about 25 gailha. In certain embodiments, the methods and compositions utilizing the compound of formula (I) or salt or ester thereof in combination with profoxydim or salt or ester thereof are used to control ECHCO, ECHCO, SCPJU or LEFCH.
In certain embodiments of the compositions and methods described herein, the compound of formula (I) or salt or ester thereof is used in combination with quizalofop-P-ethyl or carboxylic acid or carboxylate salt thereof or other ester. With regard to the compositions, in some embodiments, the weight ratio of the compound of formula (I) or salt or ester thereof to quizalofop-P-ethyl or carboxylic acid or carboxylate salt thereof or other ester is within the range of from about 1:100 to about 12:1. In certain embodiments, the weight ratio of the compound of formula (I) or salt or ester thereof to quizalofop-P-ethyl or carboxylic acid or carboxylate salt thereof or other ester is within the range of from 1:8 to about 19:1. In certain embodiments, the weight ratio of the compound of formula (1) or salt or ester thereof to quizalofop-P-ethyl or carboxylic acid or carboxylate salt thereof or other ester is within the range of from 1:6 to about 1:1. In certain embodiments, the weight ratio of the compound of formula (I) or salt or ester thereof to quizalofop-P-ethyl or carboxylic acid or carboxylate salt thereof or other ester is within the range of from about 1:12 to about 10:1. In certain embodiments, the weight ratio of the compound of formula (I) or salt or ester thereof to quizalofop-P-ethyl or carboxylic acid or carboxylate salt thereof or other ester is within the range of from about 1:6 to about 5:1. In certain embodiments, the compositions provided herein comprise the compound of formula (I) or its benzyl ester and quizalofop-P-ethyl. In one embodiment, the composition comprises the compound of formula (I) and quizalofop-P-ethyl, wherein the weight ratio of the compound of formula a) to quizalofop-P-ethyl is about 1:6 to about 5:1. In one embodiment, the composition comprises the benzyl ester of the compound of formula (I) and quizalofop-P-ethyl, wherein the weight ratio of the benzyl ester RECTIFIED (RULE 91) - ISA/US

of the compound of formula (I) to quizalofop-P-ethyl is about 1:6 to about 5:1. With respect to the methods, in certain embodiments, the methods comprise contacting the undesirable vegetation or locus thereof or applying to the soil or water to prevent the emergence or growth of vegetation a composition described herein. In some embodiments, the composition is applied at an application rate of from about 6 grams active ingredient per hectare (gai/ha) to about 400 gai/ha based on the total amount of active ingredients in the composition. In certain embodiments, the composition is applied at an application rate of from about 8 grams active ingredient per hectare (gai/ha) to about 50 gai/ha based on the total amount of active ingredients in the composition. In some embodiments, the methods comprise contacting the undesirable vegetation or locus thereof or applying to the soil or water to prevent the emergence or growth of vegetation with a compound of formula (I) or salt or ester thereof and quizalofop-P-ethyl or carboxylic acid or carboxylate salt thereof or other ester, e.g., sequentially or simultaneously. In some embodiments, the quizalofop-P-ethyl or carboxylic acid or carboxylate salt thereof or other ester is applied at a rate from about 4 gai/ha to about 100 gae/ha and the compound of formula (1) of salt or ester thereof is applied at a rate from about 2 gae/ha to about 300 gae/ha. In some embodiments, the quizalofop-P- or carboxylic acid or carboxylate salt thereof or other ester is applied at a rate from about 2 gai/ha to about 60 gai/ha and the compound of formula (I) of salt or ester thereof is applied at a rate from about 2 g acid equivalent per hectare (gae/ha) to about 70 gae/ha. In some embodiments, the quizalofop-P-ethyl or carboxylic acid or carboxylate salt thereof or other ester is applied at a rate from about 3.56 gai/ha to about 30 gai/ha and the compound of formula (I) of salt or ester thereof is applied at a rate from about 3.75 g acid equivalent per hectare (gae/ha) to about 35 gae/ha. In certain embodiments, the methods utilize the compound of formula (I), or its benzyl ester and quizalofop-P-ethyl. In one embodiment, the methods utilize the compound of formula (1) and quizalofop-P-ethyl, wherein the compound of formula (I) is applied at a rate of from about 3.75 g acid equivalent per hectare (gae/ha) to about 35 gae/ha, and quizalofop-P-ethyl is applied at a rate of about 3.56 gai/ha to about 30 gailha. In one embodiment, the methods utilize the benzyl ester of the compound of formula (1) and quizalofop-P-ethyl, wherein the benzyl ester of the compound of formula (I) is applied at a rate of from about 3.75 g acid equivalent per hectare (gae/ha) to about 17.5 gae/ha, and quizalofop-P-ethyl is applied at a rate of about 3.56 gai/ha to about 30 gai/ha. In certain embodiments, the methods and compositions utilizing the compound of formula (1) or salt or ester thereof in combination with quizalofop-P-ethyl or carboxylic acid or carboxylate salt RECTIFIED (RULE 91) - ISA/US

tlwreof or other ester are used to control 1POHE, ECHOR, CYPRO, ECHCG, AVEFA, LOLMI.j.
In certain embodiments of the compositions and methods described herein, the compound of formula (1) or salt or ester thereof is used in combination with sethoxydim or salt or ester thereof. With regard to the compositions, in some embodiments, the weight ratio of the compound of formula (I) or salt or ester thereof to sethoxydim or salt or ester thereof is within the range of from about 1:70 to about 29:1. In certain embodiments, the weight ratio of the compound of formula (I) or salt or ester thereof to sethoxydim or salt or ester thereof is within the range of from I :8 to about 2:1. I In certain embodiments, the weight ratio of the compound of formula (1) or salt or ester thereof to sethoxydim or salt or ester thereof is within the range of from about 1:61 to about 1:2. In certain embodiments, the weight ratio of the compound of formula (I) or salt or ester thereof to sethoxydim or salt or ester thereof is within the range of from about 1:120 to about 1:3. In certain embodiments, the weight ratio of the compound of formula (I) or salt or ester thereof to sethoxydim or salt or ester thereof is within the range of from about 1:54 to about 1:7.7. In certain embodiments, the compositions provided herein comprise the compound of formula (I) or its benzyl ester and sethoxydim. In one embodiment, the composition comprises the compound of formula (I) and sethoxydim, wherein the weight ratio of the compound of formula (I) to sethoxydim is about 1:54 to about 1:7.7. In one embodiment, the composition comprises the benzyl ester of the compound of formula (I) and sethoxydim, wherein the weight ratio of the benzyl ester of the compound of formula (I) to sethoxydim is about 1:27 to about 1:15.4. With respect to the methods, in certain embodiments, the methods comprise contacting the undesirable vegetation or locus thereof or applying to the soil or water to prevent the emergence or growth of vegetation a composition described herein. In some embodiments, the composition is applied at an application rate of from about 55 grams active ingredient per hectare (gai/ha) to about 825 gai/ha based on the total amount of active ingredients in the composition. In certain embodiments, the composition is applied at an application rate of from about 55 grams active ingredient per hectare (gai/ha) to about 300 gai/ha based on the total amount of active ingredients in the composition. In some embodiments, the methods comprise contacting the undesirable vegetation or locus thereof or applying to the soil or water to prevent the emergence or growth of vegetation with a compound of formula (I) or salt or ester thereof and sethoxydim or salt or ester thereof, e.g., sequentially or simultaneously.
In some embodiments, the sethoxydim or salt or ester thereof is applied at a rate from about 50 gai/ha to about 525 gal/ha and the compound of formula (0 of salt or ester thereof is applied at a SUBSTITUTE SHEET (RULE 26) rate from about 2 gae/ha to about 300 gaelha. In some embodiments, the sethoxydim or salt or ester thereof is applied at a rate from about 30 gai/ha to about 600 gai/ha and the compound of formula (I) of salt or ester thereof is applied at a rate from about 2 g acid equivalent per hectare (gae/ha) to about 45 gae/ha. In some embodiments, the sethoxydim or salt or ester thereof is applied at a rate from about 67.5 gailha to about 270 gai/ha and the compound of formula (1) of salt or ester thereof is applied at a rate from about 4.38 g acid equivalent per hectare (gae/ha) to about 17.5 gae/ha. In certain embodiments, the methods utilize the compound of formula (I), or its benzyl ester and sethoxydim. In one embodiment, the methods utilize the compound of formula (I) and sethoxydim, wherein the compound of formula (0 is applied at a rate of from about 4.38 g acid equivalent per hectare (gae/ha) to about 17.5 gae/ha, and sethoxydim is applied at a rate of about 67.5 gal/ha to about 270 gai/ha. In one embodiment, the methods utilize the benzyl ester of the compound of formula (I) and sethoxydim, wherein the benzyl ester of the compound of formula (I) is applied at a rate of from about 4.38 g acid equivalent per hectare (gae/ha) to about 8.75 gae/ha, and sethoxydim is applied at a rate of about 135 gai/ha. In certain embodiments, the methods and compositions utilizing the compound of formula (I) or salt or ester thereof in combination with sethoxydim or salt or ester thereof are used to control CYPES, CYPDI, CYPIR, SCPJU, LEFCH, FIMMI, or ECHCG.
In certain embodiments of the compositions and methods described herein, the compound of formula (I) or salt or ester thereof is used in combination with tralkoxydim or salt or ester thereof. With regard to the compositions, in some embodiments, the weight ratio of the compound of formula (0 or salt or ester thereof to tralkoxydim or salt or ester thereof is within the range of from about 1:38 to about 60:1. In certain embodiments, the weight ratio of the compound of formula (I) or salt or ester thereof to tralkoxydim or salt or ester thereof is within the range of from 1:23 to about 10:1. In certain embodiments, the weight ratio of the compound of formula (1) or salt or ester thereof to tralkoxydim or salt or ester thereof is within the range of from 1:40 to about 1:2. In certain embodiments, the compositions comprise the compound of formula (I) or its benzyl or n-butyl ester and tralkoxydim. With respect to the methods, in certain embodiments, the methods comprise contacting the undesirable vegetation or locus thereof or applying to the soil or water to prevent the emergence or growth of vegetation a composition described herein.
In some embodiments, the composition is applied at an application rate of from about 7 gams active ingredient per hectare (gai/ha) to about 375 gal/ha based on the total amount of active ingredients in the composition. In certain embodiments, the composition is applied at an SUBSTITUTE SHEET (RULE 26) application rate of from about 8 grams active ingredient per hectare (gaiiha) to about 100 gaiiha based on the total amount of active ingredients in the composition. In some embodiments, the methods comprise contacting the undesirable vegetation or locus thereof or applying to the soil or water to prevent the emergence or growth of vegetation with a compound of formula (I) or salt or ester thereof and tralkoxydim or salt thereat e.g., sequentially or simultaneously. In some embodiments, the tralkoxydim or salt or ester thereof is applied at a rate from about 5 gailha to about 75 gaila and the compound of formula (I) of salt or ester thereof is applied at a rate from about 2 gaelha to about 300 gaeiha. In certain embodiments, the methods utilize the compound of formula (I) or its benzyl or n-butyl ester and tralkoxydim are used to control AVEFA, CYPIR, KCHSC and LOI,MU.
The components of the mixtures described herein can be applied either separately or as part of a multipart herbicidal system.
The mixtures described herein can be applied in conjunction with one or more other herbicides to control a wider variety of undesirable vegetation. When used in conjunction with other herbicides, the composition can be formulated with the other herbicide or herbicides, tank mixed with the other herbicide or herbicides or applied sequentially with the other herbicide or herbicides. Some of the herbicides that can be employed in conjunction with the compositions and methods described herein include, but are not limited to: 4-CPA;
4-CPB; 4-CPP; 2,4-D; 2,4-D choline salt, 2,4-D esters and amines, 2,4-DB; 3,4-DA; 3,4-DB;
2,4-DEB; 2,4-DEP; 3,4-DP; 2,3,6-TBA; 2,4,5-1; 2,4,5-TB; acetochlor, acifluorfen, aclonifen, acrolein, alachlor, allidochlor, alloxydim, allyl alcohol, alorac, ametridione, ametryin, amibuzin, amicarbazone, amidosulfuron, aminocyclopyrachlor, aminopyralid, amiprofos-methyl, amitrole, ammonium sulfamate, anilofos, anisuron, asulam, atraton, atrazine, azafenidin, azimsulfuron, aziprotryne, barban, BCPC, beflubutamid, henazolin, bencarbazone, benfluralin, benfuresate, bensulfuron-methyl, bensulide, benthiocarb, bentazon-sodium, benzadox, benzfendizone, benzipram, benzobicyclon, benzofenap, benzofluor, benzoylprop, benzthiaz- uron, bialaphos, bicyclopyrone, bifenox, bilanafos, bispyribac-sodium, borax, bromacil, bromobonil, bromobutide, bromofenoxim, bromoxynil, brompyrazon, butachlor, butafenacil, butamifos, butenachlor, buthidazole, buthiuron, butralin, butroxydim, buturon, butylate, cacodylic acid, cafenstrole, calcium chlorate, calcium cyanamide, cambendichlor, carbasulam, carbetamide, carboxazole chlorprocarb, carfentrazone-ethyl, CDEA, CEPC, chlomethoxyfen, chloramben, chloranocryl, chlorazifop, chlorazine, chlorbromuron, chlorbufam, chloreturon, chlorfenac, chlorfenprop, chlorflurazole, chlorflurenol, chloridazon, chlorimuron, chlornitrofen, chloropon, SUBSTITUTE SHEET (RULE 26) chlorotoluron, chloroxuron, chloroxynil, chlorpropham, chlorsulfuron, chlorthal, chlorthiamid, cinidon-ethyl, cinmethylin, cinosulfuron, cisanilide, cliodinate, clofop, clomazone, clomeprop, cloprop, cloproxydim, clopyralid, cloransulam-methyl, CMA, copper sulfate, CPMF, CPPC, credazine, cresol, cumyluron, cyanatryn, cyanazine, cycloate, cyclopyrimorate, cyclosulfamuron, cycloxydim, cycluron, cyperquat, cyprazine, cyprazole, cypromid, daimuron, dalapon, dazomet, delachlor, desmedipham, desmetryn, di-allate, dicamba, dichlobenil, dichloralurea, dichlormate, dichlotprop, dichlorprop-P, diclosulam, diethamquat, diethatyl, difenopenten, difenoxuron, difenzoquat, diflufenican, diflufenzopyr, dimefuron, dimepiperate, dimethachlor, dimethametryn, dimethenamid, dimethenamid-P, dimexano, dimidazon, dinitramine, dinofenate, dinoprop, dinosam, dinoseb, dinoterb, diphenamid, dipropetryn, diquat, disul, dithiopyr, diuron, DMPA, DNOC, DSMA, EBEP, eglinazine, endothal, epronaz, EPTC, erbon, esprocarb, ethalfluralin, ethbenzamide, ethametsulfuron, ethidimuron, ethiolate, ethobenzamid, etobenzamid, ethofumesate, ethoxyfen, ethoxysulfuron, etinofen, etnipromid, etobenzanid, EXD, fenasulam, fenoprop, fenoxasulfone, fenteracol, fenthiaprop, fentrazamide, fenuron, ferrous sulfate, flamprop, flamprop-M, flazasulfuron, florasulam, fluazolate, flucarbazone, flucetosulfuron, fluchloralin, flufenacet, flufenican, flufenpyr-ethyl, flumetsulam, flumezirt, flumiclorac-pentyl, flumioxazin, flumipropyn, fluometuron, fluorodifen, fluoroglycofen, fluoromidine, fluoronitrofen, fluothiuron, flupoxam, flupropacil, flupropanate, flupyrsulfuron, fluridone, flurochloridone, fltuoxypyr, fluroxypyr-meptyl, flurtamone, fluthiacet, fomesafen, foramsulfuron, fosamine, fumiclorac, furyloxyfen, glufosinate, glufosinate-ammonium, glufosinate-P-ammonium, glyphosate salts and esters, halauxifen, halauxifen-methyl, halosafen, halosulfuron-methyl, haloxydine, hexachloroacetone, hexaflurate, hexa-zinone, imazamethabenz, imazamox, imazapic, imazapyr, imazaquin, imazosulfuron, imazethapyr, indanofan, indaziflam, iodobonil, iodomethane, iodosulfuron, iodosulfuron-ethyl-sodium, iofensulftwon, ioxynil, ipazine, ipfencarbazone, iprymidam, isocarbamid, isocil, isomethiozin, isonoruron, isopolinate, isopropalin, isoproturon, isouron, isoxaben, isoxachlortole, isoxaflutole, isoxapyrifop, karbutilate, ketospiradox, lactofen, lenacil, linuron, MAA, MAMA, MCPA esters and amines, MCPA-thioethyl, MCPB, mecoprop, mecoprop-P, medinoterb, mefenacet, mefluidide, mesoprazine, mesosulfuron, mesotrione, metam, metamitron, metazachlor, metaz.osulfuron, metflurazon, methabenzthiazuron, methalpropalin, methazole, methiobencarb, methiozolin, methiuron, methometon, methoprotryne, methyl bromide, methyl isothiocyanate, methyldymron, metobenzuron, metobromuron, metolachlor, metosulam, metoxuron, metribuzin, metsulfuron, metsulfuron-methyl, molinate, monalide, SUBSTITUTE SHEET (RULE 26) monisouron, monochloroacetic acid, monolinuron, monuron, morfamquat, MS1VLA, naproanilide, napropamide, naptalam, neburon, nicosulfuron, nipyraclofen, nitralin, nitrofen, nitrofluorfen, norflurazon, noniron, OCH, otbencarb, ortho-dichlorobenzene, orthosulfamuron, oryzalin, oxadiargyl, oxadiazon, oxapyrazon, oxasulfuron, oxaziclomefone, oxyfluorfen, paraflufen-ethyl, parafluron, paraquat, pebulate, pelargonic acid, pendimethalin, penoxsulam, pentachlorophenol, pentanochlor, pentoxazone, perfluidone, pethoxamid, phenisopham, phenmedipham, phenmedipham-ethyl, phenobenzuron, phenylmercury acetate, picioram, picolinafen, piperophos, potassium arsenite, potassium azide, potassium cyanate, pretilachlor, primisulfuron-methyl, procyazine, prodiamine, profluazol, profluralin, proglinazine, prohexadione-calcium, prometoin, prometryn, pronamide, propachlor, propanil, propaquizafop, propazine, propham, propisochlor, propoxycarbazone, propyfisulfuron, propyzamide, prosulfalin, prosulfocarb, prosulfuron, proxan, prynachlor, pydanon, pyraclonil, pyraflufen-ethyl, pyrasulfotole, pyrawgyl, pyrazolynate, pyrazosulfuron-ethyl, pyrazoxyfen, pyribenzoxim, pyributicarb, pyriclor, pyridafol, pyridate, pyfiftalid, pyriminobac, pyrimisulfan, pyrithiobac-sodium, pyroxasulfone, pyroxsulam, quinclorac, quinmerac, quinoclamine, quinonamid, rhodethanil, rimsulfuron, saflufenacil. S-metolachlor, sebuthylazine, secbumeton, siduron, simazine, simeton, simetryn, SMA, sodium arsenite, sodium azide, sodium chlorate, sulcotrione, sulfallate, sulfentrazone, sulfometuron, sulfosate, sulfosulfuron, sulfuric acid, sulglycapin, swep, SYN-523, TCA, tebutam, tebuthiuron, tefuryltrione, tembotrione, tepraloxydim, terba.cil, terbucarb, terbuchlor, terbumeton, terbuthylazine, terbutryn, tetrafluron, thenylchlor, thiaz.afluron, thiazopyr, thidiazimiin, thidiazuron, thiencarba;zone-methyl, thifensulfuron, thifensulfum-methyl, thiobencarb, tiocarbazil, tioclorim, topramezone, triafamone, tri-allate, triasulfuron, tria-ziflam, tribenuron, tribenuron-methyl, tricamba, triclopyr awhile salt, triclopyr esters and salts, tridipharie, trietazine, trifloxysulfuron, trifluralin, triflusulfuron, trifop, trifopsime, trihydroxytriazine, trimeturon, tripropindan, tritac tritosulfuron, vernolate, xylachlor and salts, esters, optically active isomers and mixtures thereof:
The compositions and methods described herein, can further be used in conjunction with glyphosate, 5-enolpynivylshikimate-3-phosphate (EPSP) synthase inhibitors, glufbsinate, glutamine synthetase inhibitors, dicamba, phenoxy auxins, pyfidyloxy auxins, synthetic auxins, auxin transport inhibitors, aryloxyphenoxypropionates, cyclohexanediones, phenylpyrazolines, acetyl CoA carboxylase (ACCase) inhibitors, imidazolinones, sulfonylureas, pyfimidinylthiobenzoates, triazolopyrimidine sulfonamides, sulfonylaminocarbonyltriawlinones, acetolactate synthase (ALS) or acetohydroxy acid SUBSTITUTE SHEET (RULE 26) synthase (AHAS) inhibitors, 4-hydroxyphenyl-pyruvate dioxygenase (HPPD) inhibitors, phytoene desaturase inhibitors, carotenoid biosynthesis inhibitors, protoporphyrinogen oxidase (PPO) inhibitors, cellulose biosynthesis inhibitors, mitosis inhibitors, microtubule inhibitors, very long chain fatty acid inhibitors, fatty acid and lipid biosynthesis inhibitors, photosystem I inhibitors, photosystem II inhibitors, triazines, and bromoxynil on glyphosate-tolerant, EPSP synthase inhibitor-tolerant, glufosinate-tolerant, glutamine synthetase inhibitor-tolerant, dicamba-tolerant, phenoxy auxin-tolerant, pyridyloxy auxin-tolerant, auxin-tolerant, auxin transport inhibitor-tolerant, aryloxyphenoxypropionate-tolerant, cyclohexanedione-tolerant, phenylpyrazoline-tolerant, ACCase-tolerant, imidazolinone-tolerant, sulfonylurea-tolerant, pyrimidinylthiobenzoate-tolerant, triazolopyrimidine-tolerant, sulfonylaminocarbonyltriazolinone-tolerant, ALS- or AHAS-tolerant, HPPD-tolerant, phytoene desaturase inhibitor-tolerant, carotenoid biosynthesis inhibitor tolerant, PPO-tolerant, cellulose biosynthesis inhibitor-tolerant, mitosis inhibitor-tolerant, microtubule inhibitor-tolerant, very long chain fatty acid inhibitor-tolerant, fatty acid and lipid biosynthesis inhibitor-tolerant, photosystem I inhibitor-tolerant, photosystem II inhibitor-tolerant, triazine-tolerant, bromoxynil-tolerant, and crops possessing multiple or stacked traits conferring tolerance to multiple chemistries and/or multiple modes of action via single and/or multiple resistance mechanisms. In some embodiments, the compound of formula (I) or salt or ester thereof and complementary herbicide or salt or ester thereof are used in combination with herbicides that are selective for the crop being treated and which complement the spectrum of weeds controlled by these compounds at the application rate employed. In some embodiments, the compositions described herein and other complementary herbicides are applied at the same time, either as a combination formulation or as a tank mix.
In some embodiments, the compositions described herein are employed in combination with one or more herbicide safeners, such as AD-67 (MON 4660), benoxacor, benthiocarb, brassinolide, cloquintocet (mexyl), cyometrinil, daimuron, dichlormid, dicyclonon, dimepiperate, disulfoton, fenchlorazole-ethyl, fenclorim, flurazole, fluxofenim, furilazole, harpin proteins, isoxadifen-ethyl, jiecaowan, jiecaoxi, mefenpyr-diethyl, mephenate, naphthalic anhydride (NA), oxabetrinil, R29148 and N-phenyl-sulfonylbenzoic acid amides, to enhance their selectivity. In some embodiments, the safeners are employed in rice, cereal, corn, or maize settings. In some embodiments, the safener is cloquintocet or an ester or salt thereof. In certain embodiments, cloquintocet is utilized to antagonize harmful effects of the compositions on rice and cereals. In some embodiments, the safener is cloquintocet (mexyl).
SUBSTITUTE SHEET (RULE 26) In some embodiments, the compositions described herein are employed in combination with one or more plant growth regulators, such as 2,3,5-tri-iodobenzoic acid, IAA, IBA, naphthaleneacetamide, a-naphthaleneacetic acids, benzyladenine, 4-hydroxyphenethyl alcohol, kinetin, zeatin, endothal, ethephon, pentachlorophenol, thidiazuron, tribufos, aviglycine, maleic hydrazide, gibberellins, gibberellic acid, abscisic acid, ancymidol, fosamine, glyphosine, isopyrimol, jasmonic acid, maleic hydrazide, mepiquat, 2,3,5-tri-iodobenzoic acid, morphactins, dichlorflurenol, flurprimidol, mefluidide, paclobutrazol, tetcyclacis, uniconazole, brassinolide, brassinolide-ethyl, cycloheximide, ethylene, methasulfocarb, prohexadione, triapenthenol and trinexapac.
In some embodiments, the plant growth regulators are employed in one or more crops or settings, such as rice, cereal crops, corn, maize , broadleaf crops, oilseed rapekanola, turf, pineapple, sugarcane, sunflower , pastures, grasslands, rangelands, fallowland, tree and vine orchards, plantation crops, vegetables, and non-crop (ornamentals) settings.
In some embodiments, the plant growth regulator is mixed with the compound of formula (I), or mixed with the compound of formula (I) and ACCase inhibitors to cause a preferentially advantageous effect on plants.
In certain embodiments, the compositions comprise or the methods utilize (a) the compound of formula 1 or agriculturally acceptable salt or ester thereof; (b) an ACCase inhibitor; and (c) a third herbicide. In some embodiments, the compositions comprise or the methods utilize a compound of Formula I or agriculturally acceptable salt or ester thereof, cyhalofop-butyl, and penoxsulam. In some embodiments, the compound of formula I or agriculturally acceptable salt or ester thereof is from about 7 to about 45 weight percent of the total composition; cyhalofop-butyl is from about 48 to about 89 weight percent of the total composition, and penoxsulam is from about 4 to about 7 weight percent of the total composition. In certain embodiments, the compound of formula I or agriculturally acceptable salt or ester thereof is from about 9 to about 28 weight percent of the total composition;
cyhalofop-butyl is from about 62 to about 88 weight percent of the total composition, and penoxsulam is from about 2 to about 10 weight percent of the total composition. In some embodiments, the compound of formula I or agriculturally acceptable salt or ester thereof, or salt or ester thereof, is applied at a rate from about 2 to about 300 gae/ha (grams acid equivalent/ha); cyhalofop-butyl salt or ester thereof is applied at a rate from about 25 to about 400 gailha (grams active ingredient/ha), and penoxsulam is applied from about I to about 50 gr al/ha (grams active ingredient/ha). In a further embodiment, the compound of formula 1 or agriculturally acceptable salt or ester thereof, is applied at a rate from about I to about 32 SUBSTITUTE SHEET (RULE 26) gae/ha; cyhalofop-butyl salt or ester thereof is applied at a rate from about 25 to about 280 gai/ha, and penoxsulam is applied from about 2 to about 35 gr ailha. In certain embodiments, the methods and compositions utilizing the compound of formula (I) or salt or ester thereof in combination with cyhalofop-butyl and penoxsulam, or salt or ester thereof, are used to control ECHCG, CYPRO and FIMMI.
In some embodiments, the compositions comprise or the methods utilize a compound of formula 1 or agriculturally acceptable salt or ester thereof, cyhalofop-butyl, and bentazon-sodium. In some embodiments, the compound of formula I or agriculturally acceptable salt or ester thereof is from about 2 to about 13 weight percent of the total composition;
cyhalofop-butyl is from about 14 to about 20 weight percent of the total composition, and bentazon-sodium is from about 73 to about 78 weight percent of the total composition. In certain embodiments, the compound of formula I or agriculturally acceptable salt or ester thereof is from about 1 to about 9 weight percent of the total composition;
cyhalofop-butyl is from about 15 to about 18 weight percent of the total composition, and bentazon-sodium is from about 78 to about 84 weight percent of the total composition. In some embodiments, the compound of Formula I, or salt or ester thereof, is applied at a rate from about 2 to about 300 gae/ha; cyhalofop-butyl is applied at a rate from about 25 to about 400 gai/ha, and bentazon-sodium is applied from about 1 to about 1,500 gr al/ha. In a further embodiment, the compound of formula I or agriculturally acceptable salt or ester thereof, is applied at a rate from about 1 to about 32 gae/ha; cyhalofop-butyl salt or ester thereof is applied at a rate from about 25 to about 280 gailha, and bentazon-sodium is applied from about 210 to about 1,200 gr ai/ha, in certain embodiments, the methods and compositions utilizing the compound of formula (I) or salt or ester thereof in combination with cyhalofop-butyl and bentazone sodium, or salt or ester thereof, are used to control ECHCG and FIMMI.
In some embodiments, the compositions comprise or the methods utilize a compound of the formula I or agriculturally acceptable salt or ester thereof, cyhalofop-butyl, and triclopyr. In some embodiments, the compound of formula I or agriculturally acceptable salt or ester thereof is from about 2 to about 20 weight percent of the total composition;
cyhalofop-butyl is from about 20 to about 22 weight percent of the total composition, and bentazon-sodium is from about 58 to about 78 weight percent of the total composition. In certain embodiments, the compound of formula I or agriculturally acceptable salt or ester thereof is from about I to about 11 weight percent of the total composition;
cyhalofop-butyl is from about 15 to about 25 weight percent of the total composition, and triclopyr is from about 64 to about 84 weight percent of the total composition. In some embodiments, the SUBSTITUTE SHEET (RULE 26) compound of Formula I, or salt or ester thereof, is applied at a rate from about 2 to about 300 gae/ha; cyhalofop-butyl is applied at a rate from about 25 to about 400 gal/ha, and triclopyr is applied from about 100 to about 840 gr ae/ha. In a further embodiment, the compound of formula I or agriculturally acceptable salt or ester thereof, is applied at a rate from about 1 to about 32 gae/ha; cyhalofop-butyl salt or ester thereof is applied at a rate from about 25 to about 280 gal/ha, and triclopyr is applied from about 210 to about 560 gr ae/ha. In certain embodiments, the methods and compositions utilizing the compound of formula (I) or salt or ester thereof in combination with cyhalofop-butyl and triclopyr, or salt or ester thereof, are used to control ECHCG and SCRIU.
In some embodiments, the compositions comprise or the methods utilize a compound of formula I or agriculturally acceptable salt or ester thereof, cyhalofop-butyl, and bispyribac-sodium. In some embodiments, the compound of formula I or agriculturally acceptable salt or ester thereof is from about 4 to about 44 weight percent of the total composition;
cyhalofop-butyl is from about 47 to about 53 weight percent of the total composition, and bispyribac-sodium is from about 9 to about 43 weight percent of the total composition. In certain embodiments, the compound of formula I or agriculturally acceptable salt or ester thereof is from about 6 to about 28 weight percent of the total composition;
cyhalofop-butyl is from about 60 to about 63 weight percent of the total composition, and bispyribac-sodium is from about 11 to about 30 weight percent of the total composition. In some embodiments, the compound of formula I, or salt or ester thereof, is applied at a rate from about 2 to about 300 gae/ha; cyhalofop-butyl is applied at a rate from about 25 to about 400 gailha, and bispyribac-sodium is applied from about 20 to about 90 gr ailha. In a further embodiment, the compound of formula I or agriculturally acceptable salt or ester thereof, is applied at a rate from about 1 to about 32 gae/ha; cyhalofop-butyl salt or ester thereof is applied at a rate from about 25 to about 280 gailha, and bispyribac-sodium is applied from about 25 to about 75 gr ai/ha. In certain embodiments, the methods and compositions utilizing the compound of formula (I) or salt or ester thereof in combination with cyhaloibp-butyl and bispyribac-sodium, or salt or ester thereof, are used to control ECHCG and SCP.IU.
In some embodiments, the compositions comprise or the methods utilize the compound of formula I, cyhalotbp-butyl, and imazamox. In some embodiments, the compound of formula I or agriculturally acceptable salt or ester thereof is from about 5 to about 44 weight percent of the total composition; cyhalofop-butyl is from about 46 to about 77 weight percent of the total composition, and imazamox is from about 10 to about 18 weight percent of the total composition. In certain embodiments, the compound of formula I

RECTIFIED (RULE 91) - ISA/US

or agriculturally acceptable salt or ester thereof is from about 8 to about 28 weight percent of the total composition; cyhalofbp-butyl is from about 58 to about 80 weight percent of the total composition, and imazamox is from about 12 to about 14 weight percent of the total composition. In some embodiments, the compound of Formula 1, or salt or ester thereof, is applied at a rate from about 2 to about 3(X) gaiiha; cyhalofop-butyl is applied at a rate from about 25 to about 400 gaitha, and imazamox is applied from about 6 to about 70 gr al/ha.
In some embodiments, the compositions comprise or the methods utilize a compound of the formula I or agriculturally acceptable salt or ester thereof, cyhalofop-butyl, and benzobicyclon. In some embodiments, the compound of formula I or agriculturally acceptable salt or ester thereof is from about 3 to about 33 weight percent of the total composition; cyhalofop-butyl is from about 32 to about 35 weight percent of the total composition, and benzobicyclon is from about 33 to about 65 weight percent of the total composition. In certain embodiments, the compound of formula I or agriculturally acceptable salt or ester thereof is from about 3 to about 19 weight percent of the total composition;
cyhalofop-butyl is from about 32 to about 42 weight percent of the total composition, and benzobicyclon is from about 39 to about 65 weight percent of the total composition. In some embodiments, the compound of Formula I, or salt or ester thereof, is applied at a rate from about 2 to about 300 gai/ha; cyhalofop-butyl is applied at a rate from about 25 to about 400 gaiiha, and benzobicyclon is applied from about 50 to about 300 gr al/ha. In a further embodiment, the compound of formula I or agriculturally acceptable salt or ester thereof, is applied at a rate from about 1 to about 32 gaelha; cyhalofop-butyl salt or ester thereof is applied at a rate from about 25 to about 280 gal/ha, and benzobicyclon is applied from about 50 to about 300 gr ai/ha. In certain embodiments, the methods and compositions utilizing the compound of formula (I) or salt or ester thereof in combination with cyhalofop-butyl and bispyribac-sodium, or salt or ester thereof, are used to control ECHCG, ECHOR
and FIMM1.
In some embodiments, the compositions comprise or the methods utilize a compound of the formula I or agriculturally acceptable salt or ester thereof, cybalofop-butyl, and quinclorac. In some embodiments, the compound of formula I or agriculturally acceptable salt or ester thereof is from about 2 to about 25 weight percent of the total composition;
cyhalofop-butyl is from about 25 to about 27 weight percent of the total composition, and quinclorac is from about 48 to about 72 weight percent of the total composition. In certain embodiments, the compound of formula I or agriculturally acceptable salt or ester thereof is from about 3 to about 14 weight percent of the total composition; cyhalofop-butyl is from about 25 to about 26 weight percent of the total composition, and quinclorac is from about 54 SUBSTITUTE SHEET (RULE 26) to about 71 weight percent of the total composition. In some embodiments, the compound of formula I, or salt or ester thereof, is applied at a rate from about 2 to about 300 gaelha;
cyhalofop-butyl is applied at a rate from about 25 to about 400 and Quinclorac is applied from about 70 to about 560 gr ai/ha.
In some embodiments, the compositions comprise or the methods utilize a compound of the formula I or agriculturally acceptable salt or ester thereof, cyhalofop-butyl, and glyphosate. In some embodiments, the compound of formula I or agriculturally acceptable salt or ester thereof is from about 1 to about 11 weight percent of the total composition;
cyhalofop-butyl is from about 11 to about 13 weight percent of the total composition, and glyphosate is from about 78 to about 86 weight percent of the total composition. In certain embodiments the compound of formula I or agriculturally acceptable salt or ester thereof is from about 1.5 to about 5.5 weight percent of the total composition; cyhalofop-butyl is from about 15 to about 11.5 weight percent of the total composition, and glyphosate is from about 83 to about 83.5 weight percent of the total composition. In some embodiments, the compound of Formula I, or salt or ester thereof, is applied at a rate from about 2 to about 300 gae/ha; cyhalofop-butyl is applied at a rate from about 25 to about 400 gailha, and glyphosate is applied from about 160 to about 2240 g In some embodiments, the compositions comprise or the methods utilize a compound of the formula I or agriculturally acceptable salt or ester thereof, cyhalofop-butyl, and glufosinate. In some embodiments, the compound of formula I or agriculturally acceptable salt or ester thereof is from about 4 to about 14 weight percent of the total composition;
cyhalofop-butyl is from about 15 to about 45 weight percent of the total composition, and glufosinate is from about 51 to about 71 weight percent of the total composition. In certain embodiments, the compound of formula I or agriculturally acceptable salt or ester thereof is from about 4 to about 7 weight percent of the total composition; cyhalofop-butyl is from about 16 to about 38 weight percent of the total composition, and glufosinate is from about 58 to about 77 weight percent of the total composition. In some embodiments, the compound of Formula I, or salt or ester thereof, is applied at a rate from about 2 to about 300 gaellia;
cyhalofop-butyl is applied at a rate from about 25 to about 400 gal/ha, and glufosinate is applied from about 28 to about 1560 gr ai/ha.
In some embodiments, the compositions comprise or the methods utilize a compound of the formula I or agriculturally acceptable salt or ester thereof, fenoxaprop, and penoxsulam. In some embodiments, the compound of formula I or agriculturally acceptable salt or ester thereof is from about 7 to about 61 weight percent of the total composition;
SUBSTITUTE SHEET (RULE 26) fenoxaprop is from about 89 to about 29 weight percent of the total composition, and penoxsulam is from about 4 to about 10 weight percent of the total composition. In certain embodiments, the compound of formula I or agriculturally acceptable salt or ester thereof is from about 9 to about 44 weight percent of the total composition; fenoxaprop is from about 41 to about 88 weight percent of the total composition, and penoxsulam is from about 3 to about 15 weight percent of the total composition. In some embodiments, the compound of Formula 1, or salt or ester thereof, is applied at a rate from about 2 to about 300 gaela;
fenoxaprop is applied at a rate from about 25 to about 140 gr ac/ha, and penoxsulam is applied from about 1 to about 50 gr al/ha.
In some embodiments, the compositions comprise or the methods utilize a compound of the formula I or agriculturally acceptable salt or ester thereof, metamifop, and penoxsulam. In some embodiments, the compound of formula 1 or agriculturally acceptable salt or ester thereof is from about 4 to about 46 weight percent of the total composition;
metamifop is from about 46 to about 94 weight percent of the total composition, and penoxsulam is from about 2 to about 8 weight percent of the total composition.
In certain embodiments, the compound of formula I or agriculturally acceptable salt or ester thereof is from about 7 to about 30 weight percent of the total composition; metamifop is from about 60 to about 90 weight percent of the total composition, and penoxsulam is from about 3 to about

10 weight percent of the total composition. In some embodiments, the compound of Formula I, or salt or ester thereof, is applied at a rate from about 2 to about 300 gaelha; metamifop is applied at a rate from about 10 to about 300 gr ac/ha, and penoxsulam is applied from about 1 to about 50 gr ai/ha. In a further embodiment, the compound of formula 1 or agriculturally acceptable salt or ester thereof, is applied at a rate from about 1 to about 32 gaelha;
metamifop salt or ester thereof, is applied at a rate from about 25 to about 100 gailha, and penoxsulam is applied from about 5 to about 35 gr ai/ha. In certain embodiments, the methods and compositions utilizing the compound of formula (I) or salt or ester thereof in combination with metamifop and penoxsulam, or salt or ester thereof, are used to control ECHCG.
In some embodiments, the compositions comprise or the methods utilize a compound of the formula I or agriculturally acceptable salt or ester thereof, profoxydim, and penoxsulam. In some embodiments, the compound of formula I or agriculturally acceptable salt or ester thereof is from about 13 to about 55 weight percent of the total composition;
profoxydim is from about 36 to about 80 weight percent of the total composition, and penoxsulam embodiments, the compound of formula I or agriculturally acceptable salt or SUBSTITUTE SHEET (RULE 26) ester thereof is from about 19 to about 39 weight percent of the total composition;
profoxydim is from about 50 to about 74 weight percent of the total composition, and penoxsulam is from about 3 to about 10 weight percent of the total composition. In some embodiments, the compound of Formula I, or salt or ester thereof, is applied at a rate from about 2 to about 300 gae/ha; profoxydim is applied at a rate from about 12 to about 200 gr ai/ha, and penoxsulam is applied from about 1 to about 50 gr ai/ha.
In some embodiments, the compositions comprise or the methods utilize a compound of the formula I or agriculturally acceptable salt or ester thereof, cyhalofop-butyl, and benfuresate. In some embodiments, the compound of formula I or agriculturally acceptable salt or ester thereof is from about 2 to about 32 weight percent of the total composition;
cyhalofop-butyl is from about 34 to about 35 weight percent of the total composition, and benfuresate is from about 33 to about 64 weight percent of the total composition. In certain embodiments, the compound of formula I or agriculturally acceptable salt or ester thereof is from about 3 to about 19 weight percent of the total composition; cyhalofop-butyl is from about 32 to about 42 weight percent of the total composition, and benfuresate is from about 39 to about 64 weight percent of the total composition. In some embodiments, the compound of Formula I, or salt or ester thereof, is applied at a rate from about 2 to about 300 gaelha;
cyhalofop-butyl, is applied at a rate from about 25 to about 400 gal/ha, and benfuresate is applied from about 50 to 300 gr aitha.
In some embodiments, the compositions comprise or the methods utilize a compound of the formula I or agriculturally acceptable salt or ester there of cyhalofop-butyl, and fentrazamide. In some embodiments, the compound of formula 1 or agriculturally acceptable salt or ester thereof is from about 5 to about 33 weight percent of the total composition;
cyhalofop-butyl is from about 35 to about 58 weight percent of the total composition, and fentrazamide is from about 32 to about 37 weight percent of the total composition. In certain embodiments, the compound of formula I or agriculturally acceptable salt or ester thereof is from about 6 to about 19 weight percent of the total composition; cyhalofbp-butyl is from about 39 to about 63 weight percent of the total composition, and fentrazamide is from about 31 to about 40 weight percent of the total composition. In some embodiments, the compound of Formula I, or salt or ester thereof, is applied at a rate from about 2 to about 300 gaelha;
cyhalofop-butyl is applied at a rate from about 25 to about 400 gai/ha, and fentrazamide is applied from about 16 to about 300 gr ai/ha.
In some embodiments, the compositions comprise or the methods utilize a compound of the formula I or agriculturally acceptable salt or ester thereof, cybalofop-butyl, and RECTIFIED (RULE 91) - ISA/US

indanofan. In some embodiments, the compound of formula I or agriculturally acceptable salt or ester thereof is from about 4 to about 33 weight percent of the total composition;
cyhalofop-butyl is from about 35 to about 48 weight percent of the total composition, and indanofan is from about 32 to about 48 weight percent of the total composition. In certain embodiments, the compound of formula I or agriculturally acceptable salt or ester thereof is from about 5 to about 19 weight percent of the total composition; cyhalofop-butyl is from about 42 to about 48 weight percent of the total composition, and indanofan is from about 39 to about 48 weight percent of the total composition. In some embodiments, the compound of Formula I, or salt or ester thereof, is applied at a rate from about 2 to about 300 gaeiha;
cyhalofop-butyl is applied at a rate from about 25 to about 400 gai/ba, and indanofan is applied from about 25 to about 300 gr ai/ha.
In some embodiments, the compositions comprise or the methods utilize a compound of the formula I or agriculturally acceptable salt or ester thereof, cybalofop-butyl, and ipfencarbazone. In some embodiments, the compound of formula! or agriculturally acceptable salt or ester thereof is from about 1 to about 27 weight percent of the total composition; cyhalofop-butyl is from about 9 to about 28 weight percent of the total composition, and ipfencarbazone is from about 45 to about 90 weight percent of the total composition. In certain embodiments, the compound of formula I or agriculturally acceptable salt or ester thereof is from about 1 to about 15 weight percent of the total composition;
cyhalofop-butyl is from about 14 to about 33 weight percent of the total composition, and ipfencarbazone is from about 52 to about 85 weight percent of the total composition. In some embodiments, the compound of Formula I, or salt or ester thereof, is applied at a rate from about 2 to about 300 gaeiha; cyhalofop-butyl is applied at a rate from about 25 to about 400 gal/ha, and ipfencarbazone is applied from about 250 to about 500 gr In some embodiments, the compositions comprise or the methods utilize a compound of the formula I or agriculturally acceptable salt or ester thereof, cyhalofop-butyl, and mefenacet. In some embodiments, the compound of formula I or agriculturally acceptable salt or ester thereof is from about 1 to about 14 weight percent of the total composition;
cyhalofop-butyl is from about 9 to about 14 weight percent of the total composition, and mefenacet is from about 72 to about 90 weight percent of the total composition. In certain embodiments, Formula I is from about 2 to about 7 weight percent of the total composition;
cyhalofop-butyl is from about 14 to about 16 weight percent of the total composition, and mefenacet is from about 77 to about 85 weight percent of the total composition. In some embodiments, the compound of Formula!, or salt or ester thereof, is applied at a rate from RECTIFIED (RULE 91) - ISA/US

about 2 to about 300 gaelha; cyhalofop-butyl is applied at a rate from about 25 to about 400 gai/ha, and mefenacet is applied from about 250 to about 1600 gr ai/ha. In a further embodiment, the compound of formula I or agriculturally acceptable salt or ester thereof, is applied at a rate from about 1 to about 32 gaelha; cyhalofop-butyl salt or ester thereof is applied at a rate from about 25 to about 280 gai/ha, and mefenacet is applied from about 75 to about 560 gr ailha.
In some embodiments, the compositions comprise or the methods utilize a compound of the formula I or agriculturally acceptable salt or ester thereof, cyhalofop-butyl, and oxazichlomafone. In some embodiments, the compound of formula I or agriculturally acceptable salt or ester thereof is from about 6 to about 43 weight percent of the total composition; cyhalofop-butyl is from about 42 to about 76 weight percent of the total composition, and oxazichlomafone is from about 11 to about 18 weight percent of the total composition. In certain embodiments, the compound of formula I or agriculturally acceptable salt or ester thereof is from about 7 to about 27 weight percent of the total composition;
cyhalofop-butyl is from about 58 to about 77 weight percent of the total composition, and oxazichlomafone is from about 14 to about 15 weight percent of the total composition. In some embodiments, the compound of Formula 1, or salt or ester thereof, is applied at a rate from about 2 to about 300 gae/ha; cyhalofop-butyl is applied at a rate from about 25 to about 400 gailha, and oxazicMomafone is applied from about 6 to about 80 g al/ha. In some embodiments, the compositions comprise or the methods utilize a compound of the formula I
or agriculturally acceptable salt or ester thereof, cyhalofop-butyl, or pretilachlor.
In some embodiments, the compound of formula I or agriculturally acceptable salt or ester thereof is from about 3 to about 22 weight percent of the total composition; cyhalofop-butyl is from about 23 to about 38 weight percent of the total composition, and pretilachlor is from about 55 to about 58 weight percent of the total composition. In certain embodiments, the compound of formula I or agriculturally acceptable salt or ester thereof is from about 3 to about 13 weight percent of the total composition; cyhalotbp-butyl is from about 26 to about 32 weight percent of the total composition, and pretilachlor is from about 61 to about 65 weight percent of the total composition. In some embodiments, the compound of Formula I, or salt or ester thereof, is applied at a rate from about 2 to about 300 gaelha; cyhalofop-butyl is applied at a rate from about 25 to about 400 gaiiha, and pretilachlor is applied from about 38 to about 750 gr ai/ha.
In some embodiments, the compound of formula I or agriculturally acceptable salt or ester thereof, cyhalotbp-butyl, and propyrisulfuron. In some embodiments, the compound of RECTIFIED (RULE 91) - ISA/US

formula I or agriculturally acceptable salt or ester thereof is from about 5 to about 42 weight percent of the total composition; cybalofop-butyl is from about 44 to about 66 weight percent of the total composition, and propyrisulfuron is from about 14 to about 29 weight percent of the total composition. in certain embodiments, the compound of formula I or agriculturally acceptable salt or ester thereof is from about 7 to about 26 weight percent of the total composition; cyhalotbp-butyl is from about 56 to about 66 weight percent of the total composition, and propyrisulfuron is from about 18 to about 27 weight percent of the total composition. In some embodiments, the compound of Formula I, or salt or ester thereof, is applied at a rate from about 2 to about 300 gae/ha; cyhalofop-butyl is applied at a rate from about 25 to about 400 gaivha, and propyrisulfuron is applied from about 11 to about 100 gr ailha.
In some embodiments, the compound of formula I or agriculturally acceptable salt or ester thereof, cyhalotbp-butyl, and pyraclonil. In some embodiments, the compound of formula I or agriculturally acceptable salt or ester thereof is from about 1 to about 33 weight percent of the total composition; cyhalofop-butyl is from about 12 to about 33 weight percent of the total composition, and pyraclonil is from about 33 to about 87 weight percent of the total composition. In certain embodiments, the compound of formula 1 or agriculturally acceptable salt or ester thereof is from about 2 to about 19 weight percent of the total composition; cyhalofop-butyl is from about 20 to about 42 weight percent of the total composition, and pyraclonil is from about 39 to about 78 weight percent of the total composition. In some embodiments, the compound of Formula I, or salt or ester thereof, is applied at a rate from about 2 to about 300 gaelha; cyhalofop-butyl is applied at a rate from about 25 to about 400 gailha, and pyraclonil is applied from about 180 to about 300 gr ai/ha.
In some embodiments, the compound of formula I or agriculturally acceptable salt or ester thereof, cyhalofop-butyl, and pyriftalid. In some embodiments, the compound of formula I or agriculturally acceptable salt or ester thereof is from about 3 to about 42 weight percent of the total composition; cyhalofop-butyl is from about 35 to about 45 weight percent of the total composition, and pyriftalid is from about 13 to about 62 weight percent of the total composition. In certain embodiments, the compound of formula I or agriculturally acceptable salt or ester thereof is from about 5 to about 27 weight percent of the total composition; cyhalofop-butyl is from about 47 to about 57 weight percent of the total composition, and pyriftalid is from about 16 to about 48 weight percent of the total composition. In some embodiments, the compound of Formula I, or salt or ester thereof, is SUBSTITUTE SHEET (RULE 26) applied at a rate from about 2 to about 300 gaelha; cyhalofop-butyl is applied at a rate from about 25 to about 400 gai/ha, and pyriftalid is applied from about 45 to about 90 gr ai/ha.
In some embodiments, the compound of formula I or agriculturally acceptable salt or ester thereof, cyhalofop-butyl, and pyrimisulfan. In some embodiments, the compound of formula I or agriculturally acceptable salt or ester thereof is from about 7 to about 46 weight percent of the total composition; cyhalofop-butyl is from about 48 to about 85 weight percent of the total composition, and pyrimisulfan is from about 6 to about 8 weight percent of the total composition. In certain embodiments, Formula I is from about 9 to about 29 weight percent of the total composition; cyhalofop-butyl is from about 63 to about 84 weight percent of the total composition, and pyrimisulfan is from about 7 to about 8 weight percent of the total composition. In some embodiments, the compound of Formula I, or salt or ester thereof, is applied at a rate from about 2 to about 300 gae/ha; cyhalofop-butyl is applied at a rate from about 25 to about 320 gal/ha, and pyrimisulfan is applied from about 2.5 to about 40 gr ai/ha.
In some embodiments, the compositions described herein are employed in combination with one or more herbicide safeners, such as AD-67 (MON 4660), benoxacor, benthiocado, brassinolide, cloquintocet (mexyl), cyometrinil, daimuron, dichlormid, dicyclonon, dimepiperate, disulfoton, fenchlorazole-ethyl, fenclorim, furilazole, fluxofenim, furilazole, hatpin proteins, isoxadifen-ethyl, jiecaowan, jiecaoxi, mefenpyr-diethyl, mephenate, naphthalic anhydride (NA), oxabetrinil, R29148 and N-phenyl-sulfonylbenzoic acid amides, to enhance their selectivity. In some embodiments, the safener is cloquintocet or an ester or salt thereof. In certain embodiments, cloquintocet is utilized to antagonize harmful effects of the compositions on rice and cereals. In some embodiments, the safener is cloquintocet (mexyl).
In some embodiments, compositions provided herein further comprise at least one agriculturally acceptable adjuvant or carrier. Suitable adjuvants or carriers should not be phytotoxic to valuable crops, particularly at the concentrations employed in applying the compositions for selective weed control in the presence of crops, and should not react chemically with herbicidal components or other composition ingredients. Such mixtures can be designed for application directly to weeds or their locus or can be concentrates or formulations that are normally diluted with additional carriers and adjuvants before application. They can be solids, such as, for example, dusts, granules, water-dispersible granules, or wettable powders, or liquids, such as, for example, emulsifiable concentrates, solutions, emulsions or suspensions. They can also be provided as a pre-mix or tank mixed.

SUBSTITUTE SHEET (RULE 26) Suitable agricultural adjuvants and carriers include, but are not limited to, crop oil concentrate; nonylphenol ethoxylate; benzylcocoalkyldimethyl quaternary ammonium salt;
blend of petroleum hydrocarbon, alkyl esters, organic acid, and anionic surfactant; C9-C11 alkylpolyglycoside; phosphated alcohol ethoxylate; natural primary alcohol (C12-C16) ethoxylate; di-sec-butylphenol EO-P0 block copolymer; polysiloxane-methyl cap;
nonylphenol ethoxylate -1- urea ammonium nitrate; emulsified methylated seed oil; tridecyl alcohol (synthetic) ethoxylate (8E0); tallow amine ethoxylate (15 E0);
PEG(400) dioleate-99.
Liquid carriers that can be employed include water and organic solvents. The organic solvents include, but are not limited to, petroleum fractions or hydrocarbons such as mineral oil, aromatic solvents, paraffinic oils, and the like; vegetable oils such as soybean oil, rapeseed oil, olive oil, castor oil, sunflower seed oil, coconut oil, corn oil, cottonseed oil, linseed oil, palm oil, peanut oil, safflower oil, sesame oil, tung oil and the like; esters of the above vegetable oils; esters of monoalcohols or dihydric, trihydric, or other lower polyalcohols (4-6 hydroxy containing), such as 2-ethyl hexyl stearate, n-butyl oleate, isopropyl myristate, propylene glycol dioleate, di-octyl succinate, di-butyl adipate, di-octyl phthalate and the like; esters of mono, di and polycarboxylic acids and the like. Specific organic solvents include, but are not limited to toluene, xylene, petroleum naphtha, crop oil, acetone, methyl ethyl ketone, cyclohexanone, trichloroethylene, perchloroethylene, ethyl acetate, amyl acetate, butyl acetate, propylene glycol monomethyl ether and diethylene glycol monomethyl ether, methyl alcohol, ethyl alcohol, isopropyl alcohol, amyl alcohol, ethylene glycol, propylene glycol, glycerine, N-methyl-2-pyrrolidinone, N,N-dimethyl alkylamides, dimethyl sulfoxide, liquid fertilizers and the like. In certain embodiments, Water is the carrier for the dilution of concentrates.
Suitable solid carriers include but are not limited to talc, pyrophyllite clay, silica, attapulgus clay, kaolin clay, kieselguhr, chalk, diatomaceous earth, lime, calcium carbonate, bentonite clay, Fuller's earth, cottonseed hulls, wheat flour, soybean flour, pumice, wood flour, walnut shell flour, lignin, cellulose, and the like.
In some embodiments, the compositions described herein further comprise one or more surface-active agents. In some embodiments, such surface-active agents are employed in both solid and liquid compositions, and in certain embodiments those designed to be diluted with carrier before application. The surface-active agents can be anionic, cationic or nonionic in character and can be employed as emulsifying agents, wetting agents, suspending agents, or for other purposes. Surfactants which may also be used in the present formulations SUBSTITUTE SHEET (RULE 26) are described, inter alia, in "McCutcheon's Detergents and Emulsifiers Annual," MC
Publishing Corp., Ridgewood, New Jersey, 1998 and in "Encyclopedia of Surfactants," Vol.
1-111, Chemical Publishing Co., New York, 1980-81. Surface-active agents include, but are not limited to salts of alkyl sulfates, such as diethanolammonium lauryl sulfate;
alkylarylsulfonate salts, such as calcium dodecylbenzenesulfonate; alkylphenol-alkylene oxide addition products, such as nonylphenol-C18 ethoxylate; alcohol-alkylene oxide addition products, such as tridecyl alcohol-C16 ethoxylate; soaps, such as sodium stearate; alkyl-naphthalene-sulfonate salts, such as sodium dibutylnaphthalenesulfonate;
dialkyl esters of sulfosuccinate salts, such as sodium di(2-ethylhexyl) sulfosuccinate; sorbitol esters, such as sorbitol oleate; quaternary amines, such as lautryl trimethylammonium chloride; polyethylene glycol esters of fatty acids, such as polyethylene glycol stearate; block copolymers of ethylene oxide and propylene oxide; salts of mono and dialkyl phosphate esters; vegetable or seed oils such as soybean oil, rapeseedlcanola oil, olive oil, castor oil, sunflower seed oil, coconut oil, corn oil, cottonseed oil, linseed oil, palm oil, peanut oil, safflower oil, sesame oil, tung oil and the like; and esters of the above vegetable oils, and in certain embodiments, methyl esters.
In some embodiments, these materials, such as vegetable or seed oils and their esters, can be used interchangeably as an agricultural adjuvant, as a liquid carrier or as a surface active agent.
Other exemplary additives for use in the compositions provided herein include but are not limited to compatibilizing agents, antifoam agents, sequestering agents, neutralizing agents and buffers, corrosion inhibitors, dyes, odorants, spreading agents, penetration aids, sticking agents, dispersing agents, thickening agents, freezing point depressants, antimicrobial agents, and the like. The compositions may also contain other compatible components, for example, other herbicides, plant growth regulants, fungicides, insecticides, and the like and can be formulated with liquid fertilizers or solid, particulate fertilizer carriers such as ammonium nitrate, urea and the like.
In some embodiments, the concentration of the active ingredients in the compositions described herein is from about 0.0005 to 98 percent by weight. In some embodiments, the concentration is from about 0.0006 to 90 percent by weight. In compositions designed to be employed as concentrates, the active ingredients, in certain embodiments, are present in a concentration from about 0.1 to 98 weight percent, and in certain embodiment's about 0.5 to 90 weight percent. Such compositions are, in certain embodiments, diluted with an inert carrier, such as water, before application. The diluted compositions usually applied to weeds SUBSTITUTE SHEET (RULE 26) or the locus of weeds contain, in certain embodiments, about 0.0006 to 10.0 weight percent active ingredient and in certain embodiments contain about 0.01 to 5.0 weight percent.
The present compositions can be applied to weeds or their locus by the use of conventional ground or aerial dusters, sprayers, and granule applicators, by addition to irrigation or paddy water, and by other conventional means known to those skilled in the art.
The described embodiments and following examples are for illustrative purposes and are not intended to limit the scope of the claims. Other modifications, uses, or combinations with respect to the compositions described herein will be apparent to a person of ordinary skill in the art without departing from the spirit and scope of the claimed subject matter.
Examples Results in Examples I, II, 111, IV VI, and VII are greenhouse trial results.
Example I. Evaluation of Postemergence Foliar-Applied Herbicidal Mixtures for Weed Control in Direct Seeded Rice Seeds or nutlets of the desired test plant species were planted in a soil matrix prepared by mixing a loam or sandy loam soil (e.g., 28.6 percent silt, 18.8 percent clay, and 52.6 percent sand, with a pH of about 5.8 and an organic matter content of about 1.8 percent) and calcareous grit in an 80 to 20 ratio. The soil matrix was contained in plastic pots with a volume of 1 quart and a surface area of 83.6 square centimeters (cm2). When required to ensure good germination and healthy plants, a fungicide treatment and/or other chemical or physical treatment was applied. The plants were grown for 8-22 days in a greenhouse with an approximate 14 hr. photoperiod which was maintained at about 29 C during the day and 26 C during the night. Nutrients (Peters Excel 15-5-15 5-Ca 2-Mg and iron chelate) were applied in the irrigation solution as needed and water was added on a regular basis.
Supplemental lighting was provided with overhead metal halide 1000-Watt lamps as necessary. The plants were employed for testing when they reached the first through fourth true leaf stage.
Treatments consisted of the acid or esters of 4-amino-3-chloro-5-fluoro-6-(4-chloro-2-fluoro-3-methoxy-phenyl)pyridine-2-carboxylic acid (Compound A), each formulated as an SC (suspension concentrate), and various herbicidal components alone and in combination.
Forms of compound A were applied on an acid equivalent basis.
Forms of compound A (compound of formula I) tested include:

RECTIFIED (RULE 91) - ISA/US

C I
II

"s=-s- ;;
C I

H3 e Compound A Acid rrk\1 Compound A Benzyl Ester Other herbicidal components were applied on an acid equivalent (ae) or active ingredient (ai) basis and included acetyl coA carboxylase (ACCase)-inhibiting herbicides (cyclohexanedione and aryloxyphenoxypropionate chemical classes) cyhalofop-butyl formulated as Clincher SF (285 gr ai/L EC), diclofop-methyl formulated as Hoelon 3EC, fenoxaprop-p-ethyl + isoxadifen-ethyl formulated as RiceStar HT (0.58 lb./gal EC) , fenoxaprop-p-ethyl + menpyr diethyl formulated as Puma lEC, metamilbp formulated as Metamifop EC, haloxyfop-methyl formulated as Gallant Supei , fluazifop-p-butyl formulated as Fusilade DX, quizalofop-p-ethyl formulated as Assure II, profoxydim formulated as Aura 20EC, clethodim applied as Intensity , sethoxydim formulated as Poast ,and tralkoxydim formulated as Achieve .
Treatment requirements were calculated based upon the rates being tested, the concentration of active ingredient or acid equivalent in the formulation, and a 12 mL
application volume at a rate of 187 Ulla.
For treatments comprised of formulated compounds, measured amounts of compounds were placed individually in 25 mL glass vials and diluted in a volume of 1.25%
(v/v) Agri-Dex crop oil concentrated to obtain 12X stock solutions. If a test compound did not dissolve readily, the mixture was warmed and/or sonicated. Application solutions were prepared by adding an appropriate amount of each stock solution (e.g., I mL) and diluted to RECTIFIED (RULE 91) - ISA/US

the appropriate final concentrations with the addition of 10 mL of an aqueous mixture of 1.25% (v/v) crop oil concentrate so that the final spray solutions contained 1.2541-0.05%
(v/v) crop oil concentrate.
For treatments comprised of technical compounds, weighed amounts can be placed individually in 25 mL glass vials and dissolved in a volume of 97:3 v/v acetone/DMSO to obtain 12X stock solutions. If a test compound does not dissolve readily, the mixture can be warmed and/or sonicated. Application solutions can be prepared by adding an appropriate amount of each stock solution (e.g., 1 mL) and diluted to the appropriate final concentrations with the addition of 10 mL of an aqueous mixture of 1.5% (v/v) crop oil concentrate so that the final spray solutions contain 1.25% (v/v) crop oil concentrate. When technical materials are used, the concentrated stock solutions can be added to the spray solutions so that the final acetone and DMSO concentrations of the application solutions are 16.2% and 0.5%, respectively.
For treatments comprised of formulated and technical compounds, weighed amounts of the technical materials can be placed individually in 25 mL glass vials and dissolved in a volume of 97:3 v/v acetone/0MS to obtain 12X stock solutions, and measured amounts of the formulated compounds can be placed individually in 25 mL glass vials and diluted in a volume of 1.5% (v/v) crop oil concentrate or water to obtain 12X stock solutions. If a test compound does not dissolve readily, the mixture can be warmed and/or sonicated.
Application solutions can be prepared by adding an appropriate amount of each stock solution (e.g., 1 mL) and diluted to the appropriate fmal concentrations with the addition of an appropriate amount of an aqueous mixture of 1.5% (v/v) crop oil concentrate so that the final spray solutions contain 1.25% (v/v) crop oil concentrate. As required, additional water and/or 97:3 v/v acetone/DMSO can be added to individual application solutions so that the final acetone and DMSO concentrations of the application solutions being compared are 8.1% and 0.25%, respectively.
All stock solutions and applications solutions were visually inspected for compound compatibility prior to application. Spray solutions were applied to the plant material with an overhead Mandel track sprayer equipped with a 8002E nozzles calibrated to deliver 187 L/ha over an application area of 0.503 m2 at a spray height of 18 to 20 inches (46 to 50 cm) above average plant canopy height. Control plants were sprayed in the same manner with the solvent blank.
The treated plants and control plants were placed in a greenhouse as described above and watered by sub-irrigation to prevent wash-off of the test compounds. After SUBSTITUTE SHEET (RULE 26) approximately 3 weeks, the condition of the test plants as compared with that of the untreated plants was determined visually and scored on a scale of 0 to 100 percent where 0 corresponds to no injury or growth inhibition and 100 corresponds to complete kill.
Colby's equation was used to determine the herbicidal effects expected from the mixtures (Colby, S.R. 1967. Calculation of the synergistic and antagonistic response of herbicide combinations. Weeds 15:20-22.) .
The following equation was used to calculate the expected activity of mixtures containing two active ingredients, A and B:
Expected = A + B - (A x B/100) A = observed efficacy of active ingredient A. at the same concentration as used in the mixture.
B = observed efficacy of active ingredient B at the same concentration as used in the mixture.
The compounds tested, application rates employed, plant species tested, and results are given in Tables 1-21.
Table 1. Synergistic Activity of Foliar-Applied Compound A Acid and Cyhalofop-Butyl Herbicidal Compositions on Weed Control in a Rice Cropping System.
Visual Weed Compound Cybalofop-Control (%) 26 A Acid butyl DAA
ISCRU
oaelha gaiTha Obs Exp 8.75 0 37 17.5 0 63 8.75 140 63 43 17.5 140 82 67 Visual Weed Compound Cyhalofop-Control (%) - 20 A Acid butyl MA
IPOHE
gaelha Dana Obs Exp 19.4 0 15 19.4 280 55 15 SUBSTITUTE SHEET (RULE 26) Table 2. Synergistic Activity of Foliar-Applied Compound A Benzyl Ester and Cyhalofop-Butyl Herbicidal Compositions on Weed Control in a Rice Cropping System.
Compound Cyp Visual Weed balofo-A Benzyl Control (%) 26 butyl Ester DAA

czac/ha gailha Ohs Exp 8.75 0 18 17.5 0 33 8.75 140 53 27 17.5 140 40 40 Table 3. Synergistic Activity of Foliar-Applied Compound A Acid and Fenoxaprop-p-ethyl -i-Isoxadifen-ethyl Herbicidal Compositions on Weed Control in a Rice Cropping System.
Fenoxaprop-Visual Weed Compound p-ethyl Control (() - 20 A Acid boxadifen-DAA
ethyl CYPDI
gaelha gailha* Obs Exp 4.38 0 80 0 17.5 0 4.38 17.5 70 80 4.38 35 99 80 4.38 70 95 80 Fenoxaprop-Visual Weed Compound p-ethyl Control (%) - 20 A Acid Isoxadifen-DAA
ethyl CYPES
oaelha gailha* Obs Exp 4.38 0 30 8.75 0 70 0 17.5 0 4.38 17.5 30 30 SUBSTITUTE SHEET (RULE 26) -- 8.75 --- i75 100 70 4.38 35 40 30 8.75 35 90 70

11 SUBSTITUTE SHEET (RULE 26) Fenoxaprop-Visual Weed Compound p-ethyl+
Control (%) - 20 A Acid Isoxadifen-DAA
ethyl SCP.TU
gaelha gailha* Obs Exp 4.38 0 60 0 17.5 50 4.38 17.5 100 80 4.38 35 95 72 4.38 70 95 72 *gailha refers to concentration of fenoxaprop-p-ethyl Table 4. Synergistic Activity of Foliar-Applied Compound A Benzyl Ester and Fenoxaprop-p-ethyl + Isoxadifen-ethyl Herbicidal Compositions on Weed Control in a Rice Cropping System.
Compound Fenoxaprop-p-Visual Weed A Benzyl ethyl +
Control CYO -20 Isoxadifen-Ester DAA
ethyl CYPES
gaelha gaitha* Obs Exp 4.38 0 70 8.75 0 80 17.5 0 95 0 17.5 0 4.38 17.5 80 70 8.75 17.5 95 80 17.5 17.5 95 95 4.38 35 80 70 8.75 35 90 80 17.5 35 99 95 4.38 70 80 70 8.75 70 95 80 17.5 70 100 95 Compound Fenoxaprop-p- Visual Weed A Benzyl ethyl + Control (%) - 20 Ester Isoxadifen- DAA.
SUBSTITUTE SHEET (RULE 26) ethyl CYPIR
gae/ha gai/he Obs Exp 4.38 0 15 0 17.5 0 4.38 17.5 70 15 4.38 35 60 15 4.38 70 70 15 *gai/ha refers to concentration of fenoxaprop-p-ethyl Table 5. Synergistic Activity of Foliar-Applied Compound A Benzyl Ester and Fenoxaprop-p-ethyl + Mefenpyr-diethyl Herbicidal Compositions on Control of Weeds Common to Rice Cropping Systems.
Fenoxaprop-p- Visual Weed Compound ethyl + Control (%) -20 A Bc.nzyl Metenpyr- DAA
Ester diethyl CYPIR
gaelha gailha* Obs Exp 8.75 0 35 0 11.5 0 8.75 11.5 80 35 8.75 23 85 35 8.75 46 50 35 2ai/ha refers to concentration of fenoxaprop-p-ethyl Table 6. Synergistic Activity of Foliar-Applied Compound A Acid and Haloxyfop-methyl Herbicidal Compositions on Control of Weeds Common to Rice Cropping Systems.
__________________________________________________ Compound Haloxyfop-Visual Weed Control (%) - 20 DAA
A Acid methyl ECHCO IPOHE
ne/ha gai/ha Obs , Exp Obs Exp 4.38 0 40 10 8.75 0 60 30 17.5 0 85 40 SUBSTITUTE SHEET (RULE 26) 0 6.75 0 - 0 -0 13.5 0 0 -i.

4.38 6.75 60 40 10 10 8.75 , 6.75 65 60 30 30 17.5 6.75 70 85 60 40 4.38 13.5 , 60 40 30 10 8.75 13.5 85 60 35 30 17.5 13.5 95 85 55 40 .
4.38 27 40 40 20 10 8.75 27 75 60 40 30 17.5 27 99 85 60 40 Visual Weed Compound Haloxyfop-Control ( /0) - 20 A Acid methyl DAA
SCRTU
. .
gae/ha oailha Obs Exp .
4.38 0 70 -8.75 0 95 -0 6.75 0 -, 0 13.5 0 -4.38 6.75 100 70 8.75 6.75 100 95 4.38 13.5 100 70 8.75 , 13.5 100 95 4.38 27 100 70 8.75 27 100 95 Table 7. Synergistic Activity of Foliar-Applied Compound A Benzyl Ester and Haloxyfop-methyl Herbicidal Compositions on Control of Weeds Common to Rice Cropping Systems.
Compound Half ) Visual Weed m v A Benzyl . ( 11- Control (%) - 20 methyl Ester MA
BRAFP
gaelha gai/ha Obs Exp 4.38 0 50 -8.75 0 70 - .....
0 6.75 0 - .
0 13.5 0 4.38 6.75 60 50 SUBSTITUTE SHEET (RULE 26) 8.75 I 6.75 70 70 4.38 13.5 70 50 8.75 13.5 85 70 CompoundHaloxfo_ Visual Weed yp A Benzyl Control (%) methyl Ester DAA
SOW
oaelha gaillia Obs Exp 4.38 0 30 8.75 0 60 0 6.75 0 0 13.5 0 4.38 6.75 100 30 8.75 6.75 100 60 4.38 13.5_ 99 30 8.75 13.5 1(X) 60 4.38 27 90 30 8.75 27 100 60 Table 8. Synergistic Activity of Foliar-Applied Compound A Acid and Metamifop Herbicidal Compositions on Weed Control in a R.ice Cropping System.
Visual Weed Compound Metamifop Control ( /0) - 24 A Acid DAA
IPOHE
uaeiba gailha Obs Exp c =
4.38 0 10 8.75 0 10 17.5 0 30 4.38 150 15 10 8.75 150 25 10 17.5 150 40 30 Table 9. Synergistic Activity of Foliar-Applied Compound A Benzyl Ester and Metamifop Herbicidal Compositions on Weed Control in a Rice Cropping System.
Compound Visual Weed A Benzyl Metamifop Control (Y0) - 22 Ester DA A

SUBSTITUTE SHEET (RULE 26) ECHCG
aaelha gai/ha Obs Exp 0 9.38 0 0 18.75 40 0 37.5 70 -8 9.38 60 35 16 9.38 80 65 32 9.38 90 80 8 18.75 85 61 16 18.75 95 79 32 18.75 99 88 8 37.5 100 81 16 37.5 100 90 32 37.5 1 94 Compound Visual Weed A Benzyl Metamifop Control (%) - 22 Ester DAA

gae/ha gai/ha Obs Exp 0 9.38 0 0 18.75 0 0 37.5 0 32 9.38 50 45 32 18.75 60 45 32 37.5 65 45 Table 10. Synergistic Activity of Foliar-Applied Compound A Acid and Fluazifop-p-butyl Herbicidal Compositions on Control of Weeds Common to Rice Cropping Systems.
Visual Weed Compound Fluazifop-p-Control (%) - 19 A Acid butyl DAA

gaelha gaelha Obs Exp 4.38 0 0 -8.75 0 10 -17.5 0 35 SUBSTITUTE SHEET (RULE 26) ______ 0 180 0 __ 4.38 45 10 0 , 8.75 45 10 10 17.5 45 50 35 4.38 9010 0 __ 8.75 90 25 10 17.5 90 15 35 .
4.38 180 10 0 8.75 180 35 10 17.5 180 40 35 Table 11. Synergistic Activity of Foliar-Applied Compound A Benzyl Ester and Fluazifop-p-butyl Herbicidal Compositions on Control of Weeds Common to Rice Cropping Systems.
Compound Fluazifop-p- Visual Weed A Ben _zyl Control (%) - 19 butyl Ester DAA
IPOHE
gaeTha gaellia Obs Exp 4.38 0 0 -8.75 0 0 -0 45 0 - .

4.38 45 10 0 8.75 45 20 0 4.38 90 15 0 8.75 90 20 0 4.38 180 20 0 8.75 180 10 0 Table 12. Synergistic Activity of Foliar-Applied Compound A Acid and Quizalofop-p-ethyl Herbicidal Compositions on Control of Weeds Common to Rice Cropping Systems.
Visual Weed Compound Quizalofop-Control (%) - 20 A Acid p-ethyl DAA
IPOHE
gaelha gailia Obs Exp 4.38 0 0 -8.75 0 20 -17.5 0 40 -SUBSTITUTE SHEET (RULE 26) . 4.---3--i(7 IIIIIIIIIIIICBIII 0 8.75 15 45 20 17.5 15 70 40 4.38 30 60 0 8.75 30 40 20 Table 13. Synergistic Activity of Foliar-Applied Compound A Benzyl Ester and Quizalofop-p-ethyl Herbicidal Compositions on Control of Weeds Common to Rice Cropping Systems.
.................................... 1 Compound Quizalofop- Visual Weed A Benzyl Control (%) - 22 yl Ester p-eth DAA , , ECHCG
gae/ha gaiiha Obs Exp . 8 0 35 - i 0 3.75 20 -0 7.5 30 8 3.75 85 48 16 3.75 65 72 32 3.75 85 84 8 7.5 85 55 16 7.5 100 76 32 7.5 100 86 Compound . , Visual Weed A Benzyl Quizalotop-Control (%) - 22 p-ethy l Ester DAA
, 1POHE
gadha gailha Obs ' Exp -, 0 1.88 0 -0 3.75 . 0 -0 7.5 0 32 1.88 60 45 . 32 , 3.75 60 45 32 7.5 50 45 SUBSTITUTE SHEET (RULE 26) Table 14. Synergistic Activity of Foliar-Applied Compound A Benzyl Ester and Diclofop-methyl Herbicidal Compositions on Control of Weeds Common to Rice Cropping Systems.
Compound Diclofop- Visual Weed A Benzyl Control (%) - 22 met hyl Ester DAA
CYPIR
gaelha gal/ha Obs Ex p Table 15. Synergistic Activity of Foliar-Applied Compound A Acid and Profoxydim Herbicidal Compositions on Weed Control in a Rice Cropping System.
Visual Weed Compound Profoxydi A A m Control (/o) - 20 cid DAA
ECHCO
gaelha gal/ha Obs Exp 4.38 0 40 0 12.5 70 4.38 12.5 99 82 Table 16. Synergistic Activity of Foliar-Applied Compound A Benzyl Ester and Profoxydim Herbicidal Compositions on Weed Control in a Rice Cropping System.
Compound Visual Weed A Benzyl Profoxydim Control ( /0) - 20 Ester DAA

SUBSTITUTE SHEET (RULE 26) LEFCH
gae/ha gailha Obs Exp 4.38 0 0 -8.75 0 10 -17.5 0 .75 --_ 0 1?.5 0 . ........

4.38 12.5 10 0 8.75 12.5 30 10 17.5 12.5 50 25 4.38 25 50 40 8.75 25 , 50 46 17.5 25 70 55 Table 17. Synergistic Activity of Foliar-Applied Compound A Acid and Sethoxydim Herbicidal Compositions on Control of Weeds Common to Rice Cropping Systems.
Visual Weed Compotmd A A Sethoxydim Control (%) - 22 cid DAA
CYPES
, gaelha mii/ha Obs Exp 4.38 0 50 8.75 0 75 -0 67.5 0 -4.38 67.5 80 . 50 8.75 67.5 80 75 4.38 135 70 50 8.75 135 100 75 4.38 270 100 50 8.75 270 70 75 _ Compound e S,thoxydim Visual Weed Control (%) - 22 DAA .
A Acid CYPDI CYPIR SCPIU
gae/h.a gailha Obs Exp Obs Exp Otis Exp 4.38 0 60 . - 15 -. _ , 0 67.5 0 - 0 - 0 t 0 135 0 - 0 - i 0 -SUBSTITUTE SHEET (RULE 26) ................ 270 0 0 __ 4.38 67.5 100 60 80 15 80 60 4.38 135 100 60 80 15 85 60 4.38 270 90 60 60 15 70 60 Table 18. Synergistic Activity of Foliar-Applied Compound A Benzyl Ester and Sethoxydim Herbicidal Compositions on Control of Weeds Common to Rice Cropping Systems.
Compound Visual Weed A Benzyl Sethoxydim Control (%) - 22 Ester DAA
ECHCG
gaiiha Obs Exp Compound Visual Weed A Benzyl Sethoxydim Control (%) - 22 Ester DAA
LEFCH
gaela gal/ha Obs Exp_____ Table 19. Synergistic Activity of Foliar-Applied Compound A Benzyl Ester and Tralkoxydim Herbicidal Compositions on Control of Weeds Common to Rice Cropping Systems.
Compound Visual Weed A Benzyl Tralkoxydim Control (%) - 22 Ester DAA

SUBSTITUTE SHEET (RULE 26) oaelha gailha Obs Exp 16 200 , 60 85 Table 20. Synergistic Activity of Foliar-Applied Compound A Benzyl Ester and Pinoxaden Herbicidal Compositions on Control of Weeds Common to Rice Cropping Systems.
Compound Visual Weed A Benzyl Pinoxaden Control (%) - 21 Ester DAA
ECHCO
oaelha gai/ha Obs Exp ------ --=

, Compound Visual Weed A Benzyl Pinoxaden Control (%) -21 Ester DAA
IPOHE
gae/ha gaiiha Obs Exp SUBSTITUTE SHEET (RULE 26) 32 0 25 ------- , Mal 15 , 10 -mil 15 20 19 . 15 60 33 MEM 30 IMIll 19 16 60 Min 10 Compound Visual Weed A Benzyl Pinoxaden Control (%) - 21 Ester DAA
SCPJU
gae/ha gai/ha Obs Exp _ 8 0 185 _ , 8 15 99 85 8 30 100 . 85 Table 21. Synergistic Activity of Foliar-Applied Compound A Benzyl Ester and Clethodim Herbicidal Compositions on Control of Weeds Common to Rice Cropping Systems.

Compound A Benzyl Clethodim Visual Weed Control (%) - 20 DAA
Ester BRAPP DIGSA
oaelha craillia .., Obs Exp Obs Exp 8 0 70 . 15 _ 32 0 90 - , _ 35 -_ SUBSTITUTE SHEET (RULE 26) Compound Visual Weed A Benzyl Clethodim Control (%) - 20 Ester DAA
CYPES
gae/ha gal/ha Obs Exp =

Compound Visual Weed A Benzyl Clethodim Control (%) - 20 Ester DAA
SCPR.1 gae/ha gal/ha Ohs Exp 8 0 _____ 70 8 280 1(X) 70 BRAPP Brachiaria platyphylla (Griseb.) Nash signalgrass, broadleaf CYPDI cyperus dWormis L. sedge, smallflower umbrella CYPES Cyperus esculentus L. nutsedge, yellow CYPIR Cyperus iria L. flatsedge, rice DIGSA Digitaria sanguinalis (L.) Scop. crabgrass, large ECHCG Echinochloa crusgalli (L.) Beauv. bamyardgrass ECHCO Echinochloa colona (L.) Link junglerice IPOHE Ipornoea hederacea Jacq. momingglory, ivyleaf ISCRU Ischaemum rugosum Salisb. saramollagrass LEFCH Leptochloa chinensis (L.) Nees sprangletop, Chinese SUBSTITUTE SHEET (RULE 26) SCPJU Schoenoplectus juncoides (Roxb.) Palla bulrush, Japanese gae/ha = grams acid equivalent per hectare = grams active ingredient per hectare Obs = observed value Exp ¨ expected value as calculated by Colby's equation DAA = days after application NT = not tested Example U. Evaluation of In-Water Applied Herbicidal Mixtures for Weed Control in Transplanted Paddy Rice Weed seeds or nutlets of the desired test plant species were planted in puddled soil (mud) prepared by mixing a shredded, non-sterilized mineral soil (50.5 percent silt, 25.5 percent clay, and 24 percent sand, with a pH of about 7.6 and an organic matter content of about 2.9 percent) and water at a 1:1 volumetric ratio. The prepared mud was dispensed in 365 mL aliquots into 16-ounce (oz.) non-perforated plastic pots with a surface area of 86.59 square centimeters (cm2) leaving a headspace of 3 centimeters (cm) in each pot. Mud was allowed to dry overnight prior to planting or transplanting. Rice seeds were planted in Sun Gra MetroMix 306 planting mixture, which typically has a pH of 6.0 to 6.8 and an organic matter content of about 30 percent, in plastic plug trays. Seedling at the second or third leaf stage of growth were transplanted into 860 nil, of mud contained in 32-oz. non-perforated plastic pots with a surface area of 86.59 cm2 4 days prior to herbicide application. The paddy was created by filling the headspace of the pots with 2.5 to 3 cm of water.
When required to ensure good germination and healthy plants, a fungicide treatment and/or other chemical or physical treatment was applied. The plants were grown for 4-22 days in a greenhouse with an approximate 14 hr. photoperiod which was maintained at about 29 C during the day and 26 C during the night. Nutrients were added as Osmocote (19:6:12, N:P:K +
minor nutrients) at 2 g per 16-oz. pot and 4 g per 32-oz. pot. Water was added on a regular basis to maintain the paddy flood, and supplemental lighting was provided with overhead metal halide 1000-Watt lamps as necessary. The plants were employed for testing when they reached the first through fourth true leaf stage.
Treatments consisted of the acid or esters of 4-amino-3-chloro-5-fluoro-6-(4-chloro-2-fluoro-3-metboxy-phenyl)pyridine-2-carboxylic acid (compound A) each formulated as an.
SC (suspension concentrate) and various herbicidal components alone and in combination.
Forms of compound A were applied on an acid equivalent basis.

RECTIFIED (RULE 91) - ISA/US

Forms of compound A (compound of formula 1) tested include:

F. ,C1 N =
=
Ci = 0 H Cv Compound A Acid N H

=
=

.14V
=
0 =

113e Compound A Benzyl Ester Other herbicidal components were applied on an acid equivalent (ae) or active ingredient (ai) basis as to normal practice used in the market, and included acetyl Co.A.
carboxyla,se (ACCase) inhibiting herbicides (cyclohexank.dione and aryloxyphenoxypropionate chemical classes) cyhalofop-butyl formulated as Clincher EC, fenoxaprop-p-ethyl isoxadifen-ethyl formulated as RiceStar HT, fenoxaprop-p-ethyl mefenpyr diethyl formulated as Puma IEC, metamifop formulated as Metamifop EC, haloxyfop-methyl formulated as Gallant Super , fluazifop-p-butyl formulated as Fusilade DX, quizalofop-p-ethyl formulated as Assure' II, profoxydim ibrmulated as Aura 20EC, and setboxydim formulated as Poast .
IS Treatment requirements for each compound or herbicidal component were calculated based upon the rates being tested, the concentration of active ingredient or acid equivalent in the formulation, an. application volume of 2 niL per component per pot, and an application area of 86.59 cm' per pot.
For formulated compounds, a measured amount was placed in an individual 100 or 200 mL glass vial and was dissolved in a volume of 1.25% (v/v) Agri-Dex crop oil concentrate to obtain application solutions. If the test compound did not dissolve readily, the mixture was warmed and/or sonicated, SUBSTITUTE SHEET (RULE 26) For technical grade compounds, a weighed amount can be placed in an individual to 200 mL glass vial and dissolved in a volume of acetone to obtain concentrated stock solutions. If the test compound does not dissolve readily, the mixture can be warmed and/or sonicated. The concentrated stock solutions obtained can be diluted with an equivalent volume of an aqueous mixture containing 2.5% (v/v) crop oil concentrate so that the final application solutions contain 1.25% (v/v) crop oil concentrate.
Applications were made by injecting with a pipetter appropriate amounts of the application solutions, individually and sequentially, into the aqueous layer of the paddy.
Control plants were treated in the same manner with the solvent blank.
Applications were made so that all treated plant material received the sam.e concentrations of acetone and crop oil concentrate.
The treated plants and control plants were placed in a greenhouse as described above and water was added as needed to maintain a paddy flood. After approximately 3 weeks the condition of the test plants as compared with that of the untreated plants was determined visually and scored on a scale of 0 to 100 peirent where 0 corresponds to no injury or growth inhibition and 100 corresponds to complete kill.
Colby's equation was used to determine the herbicidal effects expected from the mixtures (Colby, S.R. 1967. Calculation of the synergistic and antagonistic response of herbicide combinations. Weeds 15:20-22.) .
The following equation was used to calculate the expected activity of mixtures containing two active ingredients, A and B:
Expected = A + B - (A x B/100) A = observed efficacy of active ingredient A at the same concentration as used in the mixture.
B = observed efficacy of active ingredient B at the same concentration as used in the mixture.
Some of the compounds tested, application rates employed, plant species tested, and results are given in Tables 22-39.
Table 22. Synergistic Activity of 1n-Water Applications of Compound A Acid and Cyhalofop-butyl Herbicidal Compositions on Weed Control in a Rice Cropping System.
Compound Cybalofop- ,Visual Weed Control (%) 25 A Acid butyl DAA
SUBSTITUTE SHEET (RULE 26) ECHOR
gae,tha -------- ai,1ha Ohs Exp 8.75 0 0 17.5 0 0 8.75 90 100 0 17.5 90 100 0 Visual Weed Compound Cyhalofop-Control (%) - 25 A Acid butyl DAA
SCRIU
gae/lia gai/ha Ohs Exp 8.75 0 65 -17.5 , 80 8.75 90 95 65 17.5 90 95 80 8.75 180 95 65 17.5 180 95 80 Visual Weed Compound Cyhal0f0P- control (0/0 _ 19 A Acid butyl DAA
LEECH_ gaelha Ohs Exp 42.4 0 10 0 180 75 , --42.4 180 90 78 Table 23. Synergistic Activity of In-Water Applications of Compound A Benzyl Ester and Cybalofop-butyl Herbicidal Compositions on Weed Control in a Rice Cropping System.
Compoundc,,ha/01.0, Visual Weed A Benz,1 butyl Control (%) - 25 Ester DA A
ECHOR
Si SUBSTITUTE SHEET (RULE 26) gaelha gai/ha Obs Exp 8.75 0 85 17.5 0 90 8.75 90 100 85 17.5 90 100 90 Compound Visual Weed Cylialofop A Benzyl ' Control (%) - 19 butyl ---- Ester ----------------- DAA
SCPMA
gae,tha gai/ha Obs Exp Table 24. Synergistic Activity of In-Water Applications of Compound A Acid and Fenoxaprop-p-ethyl Isoxadifen-ethyl Herbicidal Compositions on Weed Control in a Rice Cropping System.
Fenoxaprop-Visual Weed Compound p-ethyl + Control (%) - 21 A Acid Isoxadifen-ethyl DAA
EC R
gac/ha gai,tha Obs Exp 8.75 0 0 17,5 0 10 .

8.75 70 100 50 .17.5 70 50 55 Fenoxa.prop-Visual Weed Compound p-ethyl + Control (%) -21 A Acid Isoxadifen-DAA
ethyl FlivLI
gaelha Obs Exp 8.75 0 20 SUBSTITUTE SHEET (RULE 26) 8.75 ------------ 35 100 20 8.75 70 60 20 Fenoxaprop-Visual Weed Compound p-ethyl + Control (%) - 71 A Acid Isoxadifen-DAA
ethyl SCRIU
gae/ha gailha Obs Exp 8.75 0 65 17.5 0 90 8.75 35 80 65 ¨
17.5 35 99 90 8.75 70 85 65 17.5 70 95 90 Table 25. Synergistic Activity of In-Water Applications of Compound A Benzyl Ester and Fenoxaprop-p-ethyl + Isoxadifen-ethyl Herbicidal Compositions on Weed Control in a Rice Cropping System.
Compound A Benzyl Fenoxaprop-p-ethyi Visual Weed Control CYO - 21 Ester Isoxadifen-ethyl DAA

gae/ha gailha Obs 4.38 0 0 8.75 0 10 17.5 0 60 4.38 70 111$
8.75 70 100 MI1M
17.5 70 100 80 Fenoxaprop-Compound visual weed A Benzvl p-cthYI -1- Control (%) - 21 isoxadifen-Ester DAA
ethyl CY-PRO
gae/ha =Ohs Exp 4.38 0 20 SUBSTITUTE SHEET (RULE 26) ----- 4.38 35 --------- 99 ----- 20 4.38 70 50 20 Table 26. Synergistic Activity of In-Water Applications of Compound A Acid and Fenoxaprop-p-ethyl Mefenpyr-diethyl Herbicidal Compositions on Control of Weeds Common to Rice Cropping Systems.
Fenoxaprop-p-Visual W-eed Compound ethyl +
Control (%) - 21 A Acid Mefenpyr DAA
diethyl ECHOR
gae/ha gaiiha Obs Exp 10.6 0 0 42.4 0 15 -10.6 23 25 0 21.2 23 15 15 42.4 23 40 15 Table 27. Synergistic Activity of In-Water Applications of Compound A Benzyl Ester and Fenoxaprop-p-ethyl Mefenpyr-diethyl Herbicidal Compositions on Control of Weeds Common to Rice Cropping Systems.
Fenoxaprop-p-Compound Visual Weed e A Benzyl thyl + Control (%) - 21 Mefenp2,,,,r-Ester DAA
diethyl ECHOR
gae/ha gai/ha Ohs Exp SUBSTITUTE SHEET (RULE 26) Table 28. Synergistic Activity of in-Water Applications of Compound A Acid and Haloxyfop-methyl Herbicidal Compositions on Control of Weeds Common to Rice Cropping Systems.
Visual Weed Compound Haloxyfop-Control (%) - 20 A Acid methyl DA.A
SCRIU
gae/ha gailha Ohs Exp 8.75 . 0 70 17.5 0 95 -35 0 95 , -, 0 13.5 0 -8.75 . 13.5 90 µ 70 17.5 13.5 95 95 _ 35 13.5 95 95 8.75 27 95 70 17.5 27 100 95 Table 29. Synergistic Activity of In-Water Applications of Compound A Benzyl Ester and Haloxyfop-methyl Herbicidal Compositions on Control of Weeds Common to Rice Cropping Systems Compound , [-faloxylop- Visual Weed A Benzyi Control (%) - 20 methyl Ester DAA
CYPRO
gaelha gailha Ohs Exp 4.38 0 50 -8.75 0 100 -17.5 0 100 -0 . 13.5 0 µ --4.38 13.5 75 50 8.75 13.5 95 100 17.5 13.5 100 100 4.38 , 27 80 50 8.75 77 95 100 _ 17.5 27 100 100 SUBSTITUTE SHEET (RULE 26) Table 30. Synergistic Activity of in-Water Applications of Compound A Acid and Metantifop Herbicidal Compositions on Weed Control in a Rice Cropping System, Compound _ Metamitop Visual Weed Control (%) -21 DAA.
A Acid FIMMI
SCPMA
gaelha gai/ba Obs Exp Obs Exp Table 31. Synergistic Activity of 1n-Water Applications of Compound A Benzyl Ester and Metamifop Herbicidal Compositions on Weed Control in a Rice Cropping System, Compound Visual Weed A Benzyl Metamifop Control (%) - 21 Ester DAA
SCRIU
0-ac/ha gailha. Obs Exp 4.38 , 0 70 4.38 75 99 70 4.38 150 100 70 Compound Visual Weed A Berrzyl Metamifop Control (A) - 21 Ester . DAA
ECHOR
gae/ha gai/ha Obs Exp Table 32. Synergistic Activity of In-Water Applications of Compound A Acid and Fluazifop-p-butyl Herbicidal Compositions on Control of Weeds Common to Rice Cropping Systems.

SUBSTITUTE SHEET (RULE 26) Visual Weed Compound Fluazifop-P-Control (%) A Acid butyl DAA
ECHOR
gae/ha gae/ha Ohs Exp 8.75 0 10 17.5 0 15 8.75 90 45 33 17.5 90 15 36 Visual Weed Compound Fluazifop-P-Control (%) -21.
A Acid butyl DAA
CYPRO
gae/ha gae/ha Ohs Exp 8.7.5 0 0 17.5 0 30 8.75 90 70 0 17.5 90 30 30 8.75 180 20 0 17.5 180 20 30 Table 33. Synergistic Activity of In--Water Applications of Compound A Benz,T1 Ester and Fluazifop-p-butyl Herbicidal Compositions on Control of Weeds Common to Rice Cropping Systems.
Compound -Visual Weed Fluazifop-A Benz.y1 - Control (%) - 2.1 P-butl Ester y DAA
ECHOR
gae/ha gaiiha Ohs Exp 8+ 0 0 4.5 0 SUBSTITUTE SHEET (RULE 26) Table 34. Synergistic Activity of In-Water Applications of Compound A Acid and Quizalof.op-p-ethyl Herbicidal Compositions on Control of Weeds Common to Rice Cropping Systems.
Visual Weed Compound Quizalofop-Control (%) - 21 A Acid p-ethyl DAA
ECHOR
gac/ha gai/ha Obs Exp 17.5 , 0 25 17.5 15 50 25 17.5 30 60 70 Visual Weed Compound Quizalofop-Control (%) - 21 A Acid p-ethyl DAA
CYPRO
0-aelha gai/ha , Obs Exp =
8.75 0 0 8.75 15 20 0 8.75 30 20 0 Table 35. Synergistic Activity of In-Water Applications of Compound A Benzyl Ester and Quizalofop-p-ethyl Herbicidal Compositions on Control of Weeds Common to Rice Cropping Systems.
Compound Qp-A Benzyl p-ethyl u'rzalofb - Visual Weed Control (%) -Ester ECHCG ECHOR
gaelha gailha Obs Exp Obs Exp SUBSTITUTE SHEET (RULE 26) 4.38 0 ----- 15 0 8.75 , 0 20 15 17.5 0 75 10 4.38 15 100 58 60 8.75 , 100 60 30 15 17.5 15 100 88 50 10 4.38 30 100 100 100 60 8.75 30 100 100 100 66 17.5 30 100 100 100 64 Table 36. Synergistic Activity of In-Water Applications of Compound A Acid and Profoxydim Herbicidal Compositions on Control of Weeds Common to Rice Cropping Systems.
Visual Weed Compound Profoxydim Control (%) -21 A Acid DAA
LEECH
gaelha Obs Exp 17.5 =MB

17.5 100 MI
Visual Weed Compound Profoxvdirri Control (%) - 22 A Acid DAA
ECHCCi gaelta pi/ha. Obs Exp 16+ 0 20 Visual Weed Compound.
Profoxydim Control (%) - 22 A Acid DAA
SCRIU
gae/Ita Obs 1 Exp SUBSTITUTE SHEET (RULE 26) Table 37. Synergistic Activity of in-Water Applications of Compound A Benzyl Ester and Profoxydim Herbicidal Compositions on Control of Weeds Common to Rice Cropping Systems.
---------------------Compound Visual Weed A Benzyl Profoxydim Control (%) - 21 Ester DAA
ECHOR
gae/ha gai/ha 1.111111=
4,38 =I= 0 8.75 0 15 III
17.5 0 10 4.38 MEM 30 0 8.75 =11= 100 15 Compound Visual Weed A Benzyl Profoxydim Control (%) - 22.
Ester DAA
ECITCG
gae/ha gai/ha Ohs Exp 8 + 50 100 65 16 , 50 100 77 Table 38. Synergistic Activity of In-Water Applications of Compound A Acid and Sethoxydim Herbicidal Compositions on Control of Weeds Common to Rice Cropping Systems.
Compound Visual Weed Sethoxydim Control (%) -21 A Acid DAA
SUBSTITUTE SHEET (RULE 26) _aelha gailha Obs Ex =
o MEM 112111111111111 8.75 135 100 60 8.75 270 100 44 Visual Weed Compound A Acid Sethoxydim Control (%) -SCPIU
gaelha gailta Obs Exp 8.75 0 65 17.5 0 90 8.75 135 95 65 17.5 _ 135 100 90 Table 39. Synergistic Activity of In-Water Applications of Compound A Benzyl Ester and Setboxydim Herbicidal Compositions on Control of Weeds Common to Rice Cropping Systems.
Compound Visual Weed A Benzyl Sethoxydim Control (%) - 21 Ester DAA
ECHCG
gaelha gailha Obs Exp 4.38 0 15 8.75 0 60 4.38 135 75 66 8.75 135 100 84 CYPRO Cyperus rotundus L. nutsedge, purple ECHCG Echinochloa crusgalli (L.) Beauv. bamyardgrass ECHOR Echinochloa oryzoides (Ard.) Fritsch watergrass, early FIMMI Fimbristylis miliacea (L.) Vahl fringerush, globe LEFCH Leptochloa chinensis (L.) Nees sprangletop, Chinese SCPJU Schoenoplectus juncoides (Roxb.) Palla bulrush, Japanese SCPMA Bolboschoenus marithnus (L) Palla or Schoenoplectus Mari 111111IS (L.) Lye clubrush, sea SUBSTITUTE SHEET (RULE 26) gae/ha = grams acid equivalent per hectare gai/ha = grams active ingredient per hectare Obs = observed value Exp = expected value as calculated by Colby's equation DAA = days after application Example III. Evaluation of Postemergence Foliar-Applied Herbicidal Mixtures for Control of Weeds Common to Row Crops such as Corn and Soybeans Seeds or nutlets of the desired test plant species were planted in a soil matrix prepared by mixing a loam or sandy loam soil (e.g., 28.6 percent silt, 18.8 percent clay, and 52.6 percent sand, with a pH of about 5.8 and an organic matter content of about 1.8 percent) and calcareous grit in an 80 to 20 ratio. The soil matrix was contained in plastic pots with a surface area of 84.6 square centimeters (cm2) and a volume of 560 cubic centimeters (cm3).
When required to ensure good germination and healthy plants, a fungicide treatment and/or other chemical or physical treatment was applied. The plants were grown for 7-31 days (d) in a greenhouse with an approximate 15 hour (h) photoperiod which was maintained at about 23-29 C during the day and 22-28 C during the night. Nutrients (Peters Excel Ca 2-Mg) and water were added on a regular basis and supplemental lighting was provided with overhead metal halide 1000-Watt lamps as necessary. The plants were employed for testing when they reached the first, second, or third true leaf stage.
Treatment requirements were calculated based upon the rates being tested, the concentration of active ingredient or acid equivalent in the formulation, and a 12 mL
application volume at a rate of 187 L/ha.
Treatments consisted of the acid or esters of 4-amino-3-chloro-5-fluoro-6-(4-chloro-2-fluoro-3-methoxy-phenyl)pyridine-2-carboxylic acid (Compound A), each formulated as an SC (suspension concentrate), and various herbicidal components alone and in combination.
Forms of compound A were applied on an acid equivalent basis.
Forms of compound A (compound of formula I) tested include:

SUBSTITUTE SHEET (RULE 26) F Cl =
<
OH = N = =

Ci H3 c<
Compound A Acid F CI
=
N-5,-;;" 0 = 0 Cr/ = =
Compound A Ben2y-1 Ester 5 Other herbicidal components were applied on an acid equivalent basis and included acetyl coA carboxylase (ACCase)-inhibiting herbicide (cyclohexanedione and alyloxyphen.oxypropionate chemical classes) quizalofop-p-ethyl formulated as Assure For treatments comprised of formulated compounds, measured amounts of compounds were placed individually in 25 triL glass vials and diluted in a volume of 1.5%
10 (v/v) Agri-Dex crop oil concentrated to obtain 6X stock solutions. If a test compound did not dissolve readily, the mixture was warmed and/or sonicated, Application solutions were prepared by adding an appropriate amount of each stock solution (typically 2 mL) and diluted to the appropriate final concentrations with the addition of an appropriate amount of 1.5% (vy) crop oil concentrate and an appropriate amount of water so that the final spray 15 solutions contained 1.25+/-0.05% (v/v) crop oil concentrate.
For treatments comprised of technical compounds, weighed amounts can be placed individually in 25 mt.. glass vials and dissolved in a volume of 97:3 v/v acetoneiDMS0 to obtain 12X stock solutions. If a test compound does not dissolve readily, the mixture can be warmed and/or sonicated, Application solutions can be prepared by adding an appropriate 20 amount of each stock solution (e.g., 1 mL) and diluted to the appropriate final concentrations with the addition of an appropriate amount of 1.5% (v/v) crop oil concentrate and an appropriate amount of water so that the final spray solutions contain 1.25%
(WV) crop oil SUBSTITUTE SHEET (RULE 26) concentrate. When technical materials are used, the concentrated stock solutions can be added to the spray solutions so that the final acetone and DMSO concentrations of the application solutions are 16.2% and 0.5%, respectively.
For treatments comprised of formulated and technical compounds, weighed amounts of the technical materials can be placed individually in 25 mL glass vials and dissolved in a volume of 97:3 v/v acetone/DMSO to obtain 6X stock solutions, and measured amounts of the formulated compounds can be placed individually in 25 mL glass vials and diluted in a volume of 1.5% (v/v) crop oil concentrate or water to obtain 6X stock solutions. If a test compound does not dissolve readily, the mixture can be warmed and/or sonicated.
Application solutions can be prepared by adding an appropriate amount of each stock solution (e.g., 2 mL) and diluted to the appropriate fmal concentrations with the addition of an appropriate amount of an aqueous mixture of 1.5% (v/v) crop oil concentrate so that the final spray solutions contained 1.25% (v/v) crop oil concentrate. When required, additional water and/or 97:3 v/v acetone/DMSO can be added to individual application solutions so that the final acetone and DMSO concentrations of the application solutions being compared are 16.2% and 0.5%, respectively.
All stock solutions and applications solutions were visually inspected for compound compatibility prior to application. Compound requirements are based upon a 12 mL
application volume at a rate of 187 liters per hectare (L/ha). Formulated compounds were applied to the plant material with an overhead Mandel track sprayer equipped with 8002E
nozzles calibrated to deliver 187 L/ha over an application area of 0.503 square meters (m2) at a spray height of 18 to 20 inches (46 to 50 cm) above the average plant canopy height.
Control plants were sprayed in the same manner with the solvent blank.
The treated plants and control plants were placed in a greenhouse as described above and watered by sub-irrigation to prevent wash-off of the test compounds. After approximately 2 weeks, the condition of the test plants as compared with that of the untreated plants was determined visually and scored on a scale of 0 to 100 percent where 0 corresponds to no injury or growth inhibition and 100 corresponds to complete kill.
Colby's equation was used to determine the herbicidal effects expected from the mixtures (Colby, S.R. 1967. Calculation of the synergistic and antagonistic response of herbicide combinations. Weeds 15:20-22.) .
The following equation was used to calculate the expected activity of mixtures containing two active ingredients, A and B:
Expected = A + B - (A x B/100) SUBSTITUTE SHEET (RULE 26) A = observed efficacy of active ingredient A at the same concentration as used in the mixture.
B = observed efficacy of active ingredient B at the same concentration as used in the mixture.
Some of the compounds tested, application rates employed, plant species tested, and results are given in Tables 40-41.
Table 40. Synergistic Activity of Foliar-Applied Compound A Acid and Quizalofop-p-ethyl Herbicidal Compositions on Control of Weeds Common to Row Crops Such as Corn and Soybean Cropping Systems.
Visual Weed Compound Quizalofop-Control (%) - 14 A Acid p-ethyl DAA
AVEFA
gaelha gaelha Obs Exp 3.75 0 0 7.5 0 0 0 14.25 40 3.75 14.25 85 40 7.5 14.25 70 40 15 14.25 55 40 Visual Weed Compound Quizalofop-Control (%) - 14 A Acid p-ethyl DAA
LOLMU
gae/ha gae/ha Obs Exp 3.75 0 0 7.5 0 10 0 3.56 0 o 7.125 60 3.75 3.56 50 0 7.5 3.56 30 10 15 3.56 40 10 3.75 7.125 70 60 7.5 7.125 80 64 15 7.125 70 64 SUBSTITUTE SHEET (RULE 26) Table 41. Synergistic Activity of Foliar-Applied Compound A Benzyl Ester and Quizzlofop-p-ethyl Herbicidal Compositions on Weeds Common to Row Crops Such as Corn and Soybean Cropping Systems.
...........................
CompoundVisual Weed Quizalofop-A Benzyl Control (%) - 14 p-e yl th Ester DAA
AV EFA
oaelha oaelha Oh Exp 3.75 0 10 7.5 0 0 0 14.25 40 3.75 14.25 75 46 7.5 14.25 99 40 15 14.25 40 46 Compound . Visual Weed Quizalofop-A Benzyl Control (%) - 14 p-ethyl Ester DAA
LOLMU
gae/ha gae/ha Obs Exp 3.75 0 0 7.5 0 10 0 3.56 0 0 7.125 60 3.75 3.56 60 0 7.5 3.56 40 10 15 3.56 35 10 3.75 7.125 70 60 7.5 7.125 75 64 15 7.125 80 64 AVEFA Avena fatua L. oat, wild LOLMLI Lolium multiflorunt Lam. ryegrass, Italian 10 gae/ha = grams acid equivalent per hectare gai/ha = grams active ingredient per hectare Obs = observed value Exp = expected value as calculated by Colby's equation SUBSTITUTE SHEET (RULE 26) D.kA = days after application Example IV. Evaluation of Postemergence Herbicidal Activity of Mixtures in Cereal Crops in the Greenhouse.
Seeds of the desired test plant species were planted in Sun Gro MetroMix 306 planting mixture, which typically has a pH of 6.0 to 6.8 and an organic matter content of about 30 percent, in plastic pots with a surface area of 103.2 square centimeters (cm2). When required to ensure good germination and healthy plants, a fungicide treatment and/or other chemical or physical treatment was applied. The plants were grown for 7-36 days in a greenhouse with an approximate 14 hour photoperiod which was maintained at about 18 C
during the day and about 17 C during the night. Nutrients and water were added on a regular basis and supplemental lighting was provided with overhead metal halide 1000-Watt lamps as necessary. The plants were employed for testing when they reached the second or third true leaf stage.
Treatments consisted of the benzyl ester of 4-amino-3-chloro-5-fluoro-6-(4-chloro-2-fluoro-3-methoxy-phenyl)pyridine-2-carboxylic acid (Compound A), formulated as an SC, a second cereal herbicide alone and then both in combination.
Forms of compound A (compound of formula I) tested include:
NH, CI
I ." 0 N
CI F

Compound A Benzyl Ester Other herbicidal components were applied on an active ingredient basis and included acetyl-CoA carboxylase (ACCase)-inhibiting herbicides clodinafop-propargyl, fenoxaprop-P-ethyl, pinoxaden and tralkoxydim.
Measured aliquots of benzyl ester of 4-amino-3-chloro-5-fluoro-6-(4-chloro-2-fluoro-3-methoxy-phenyl)pyridine-2-carboxylic acid (Compound A) were placed in 25 milliliter (mL) glass vials and diluted in a volume of 1.25% (v/v) Agri-Dee crop oil concentrate to obtain stock solutions. Compound requirements are based upon a 12 mL
application volume at a rate of 187 liters per hectare (L/ha). Spray solutions of the second cereal herbicide and experimental compound nu xtures were prepared by adding the stock solutions to the SUBSTITUTE SHEET (RULE 26) appropriate amount of dilution solution to form 12 mL, spray solution with active ingredients in two- and three-way combinations. Formulated compounds were applied to the plant material with an overhead Mandel track sprayer equipped with an 8002E nozzle calibrated to deliver 187 Uha over an application area of 0.503 square meters (m2) at a spray height of 18 inches (46 cm) above average plant canopy. Control plants were sprayed in the same manner with the solvent blank.
The treated plants and control plants were placed in a greenhouse as described above and watered by sub-irrigation to prevent wash-off of the test compounds. After 20-22 days, the condition of the test plants as compared with that of the control plants was determined visually and scored on a scale of 0 to 100 percent where 0 corresponds to no injury and 100 corresponds to complete kill.
Colby's equation was used to determine the herbicidal effects expected from the mixtures (Colby, S.R. 1967. Calculation of the synergistic and antagonistic response of herbicide combinations. Weeds 15:20-22.) .
The following equation was used to calculate the expected activity of mixtures containing two active ingredients, A and B:
Expected = A + B - (A x B/100) A = observed efficacy of active ingredient A at the same concentration as used in the mixture.
B = observed efficacy of active ingredient B at the same concentration as used in the mixture.
The compounds tested, application rates employed, plant species tested, and results are given in Tables 42-45.
Table 42. Synergistic Activity of Foliar-Applied Compound A Benzyl Ester and Clodinafop-propargyl Herbicidal Compositions on Weed Control in a Cereals Cropping System.
Compound Clodnofop- Visual Weed Control A Benzyl i propargyl (%) -21 DAA
Ester 1..01.:MLE KCHSC
gaiiha gailha Obs Exp Obs Exp SUBSTITUTE SHEET (RULE 26) Compound Clodinofop-A Benzyl Visual Weed Control (%) -21 DAA
propargyl Ester PHAMI APESV ALOMY
gailha gai/ha Ohs Exp Obs Exp Ohs Exp 5 , 0 0 - 0 - 0 --t +

10 , 15 73 48 55 15 88 80 -t Table 43. Synergistic Activity of Foliar-Applied Compound A Benzyl Ester and Fenoxaprop-5 P-ethyl Herbicidal Compositions on Weed Control in a Cereals Cropping System.
Compound Eenoxaprop-A Benzyl Visual Weed Control (%) - 21 DAA
P-ethyl Ester KCHSC PHAMI APESV
gai/ha gailha Ohs Exp Ohs Exp Obs Exp 5 +
Li 68 30 10 10 63 50 Table 44. Synergistic Activity of Foliar-Applied Compound A Beuzyl Ester and Pinoxaden Herbicidal Compositions on Weed Control in a Cereals Cropping System, Compound A Benzyl Pinoxaden Visual Weed Control (A) -Ester KCHSC PHAMI

SUBSTITUTE SHEET (RULE 26) 2.-,a.i/ha ----- gal/ha Obs Exp Obs Exp 0 30 .. 0 _ .

. _ +
5 30 µ 75 32 94 94 _ Table 45. Synergistic Activity of Foliar-Applied Compound A Benzyl Ester and Tralkoxydim Herbicidal Compositions on Weed Control in a Cereals Cropping System.
5 .
Compound A Benzyl Tralkoxydim Visual Weed Control (%) - 21 [)AA
Ester + _ AVEF.A LOLNIU KCHSC
+ _ 4, esi/ha oaiiha Obs Exp Obs Exp Obs Exp :.-, .
0 100 99 96 ... 0 +
550 µ 95 78 µ 95 86 55 28 . , , A-LON/1Y Alopecurus myosuroides Hads.
blackgrass APESV Apera spica-venti (=L.) Bea.uv. windgrass AVEFA Avena fatua L. wild oat 10 KCHSC Kochia scoparia (L.) Schrad.
kochia LOTN4U Loll= muNflorum Lam. tyegrass, Italian PHANI1 Phalaris minor Retz. Canarygrass, littleseed ga.elha ¨ grams acid equivalent per hectare gai/ha .¨ grams active ingredient per hectare Obs = observed value Exp = expected value as calculated by Colby's equation DAA = days after application SUBSTITUTE SHEET (RULE 26) Example V. Evaluation of Post-emergence Herbicidal Activity of Mixtures Applied Under Field Conditions to Seeded Rice Multiple field trials were conducted under commercial grower field conditions in Tolima, Colombia; Thessaloniki, Greece; Bianze and Copiano, Italy; and Humphrey, Arkansas, USA. Trials sites were located in commercially grown fields of direct-seeded rice (Olyza saliva) using standard herbicide small plot research methodology. Plots varied from 2 to 3 meter (m) x 5 to 8 m (width x length) with 4 replicates per treatment.
The rice crop was grown using normal cultural practices for fertilization, seeding, watering, flooding and maintenance to ensure good growth of the crop and the weeds.
All treatments in the field trials were applied using a backpack compressed air/gas sprayer with flat fan nozzles (80 or 110 ) calibrated to apply 187 to 300 L/ha spray volume at approximately 200-400 kPa nozzle pressure. Commercially available products of cyhalofop-butyl (Clincher 1.80K, Clincher 200K, and Clincher SF (285 gr ai/L
EC)) were mixed in water at appropriate formulated product rates to achieve the desired rates based on a unit area of application (hectare) to achieve the desired rates as shown.
Treatments were rate at 19 to 58 days after application (DAA) as compared to the untreated control plants. Visual weed control was scored on a scale of 0 to 100 percent where 0 corresponds to no injury and 100 corresponds to complete kill.
All treatment results, both for the single product and mixtures, are an average of 4 replicates. The trial sites had naturally occurring populations of weeds. The weed spectrum included, but was not limited to, rice flatsedge (C:vperus iria, CYPIR);
smallflower umbrellaplant (C)perus difformis, CYPDI), junglerice (Echinochloa colona, ECHCO), barnyardgrass (Echinochloa crus-galli, ECHCG); multiple Echinochloa species in the same field (ECHSS), grasslike fimbristylis (Fimbristylis miliacea, FIMMD; ricefield bulrush (Schoenoplectus mucronatus, SCPMU) and hemp Sesbania (Sesbania exaitata, SEBEX). All synergistic interactions were significant at the P>0.01 level.
Some of the compounds tested, application rates employed, plant species tested, and results are given in Tables 46-48.
Table 46. Synergistic Activity of Foliar-Applied Compound A Benz.y1 Ester and Cybalofop-butyl Herbicidal Compositions on Weed Control in a Rice Cropping System when evaluated 19 DAA (Days After Application) in Tolima, Colombia.

SUBSTITUTE SHEET (RULE 26) Visual Weed Control (%) - 19 DAA
Compound c vhaiefo4) -A Benzyl ' but,',,I.
Ester gaelha gai/ha Obs+ Exp Obs Exp Obs Exp 17 0 , 69 - 76 - - -, 0 190- ., 16 -+
-Table 47, Synergistic Activity of Foliar-Applied Compound A Benzyl Ester and Cyhalofop-butyl Herbicidal Compositions on Weed Control in a Rice Cropping System when evaluated 7DAA (Days After Application) in Humphrey, Arkansas, USA..
Visual Weed Compound Cyhalofop- Control (Y0) - 7 .A Benzyl =
butyl DAA
Ester SEBEX¨ ------ --gae/ha gai/ha Ohs Exp 24 . 280 90 80 0 , 280 , 0 -Table 48. Synergistic Activity of Foliar-Applied Compound A Benzyl Ester and Cyhalofop-butyl Herbicidal Compositions on Weed Control in a Rice Cropping System when evaluated 55 to 58 DAA (Days After Application) in Greece (CYPD1 and ECHCG) and Italy (ECHSS
and SCPMU).
Compound Cyhalofop- Visual Weed Control (%) ¨ 55-A Benzyl ' butyl Ester SUBSTITUTE SHEET (RULE 26) CYPDI ECHCG ECHSS SCPIvIU
gaetha gai/ha Obs Exp Obs Exp Obs Exp Obs Exp 24 0 Si 6 40 27 Example V. Evaluation of Postemergence Foliar-Applied Ternary Herbicidal Mixtures for Weed Control in Direct Seeded Rice Seeds or nutlets of the desired test plant species were planted in a soil matrix prepared by mixing a sandy loam or loam soil (e.g., 32 percent silt, 23 percent clay, and 45 percent sand, with a pH of about 6.5 and an organic matter content of about 1.9 percent) and calcareous grit in an 80 to 20 ratio. The soil matrix was contained in plastic pots with a volume of 1 quart and a surface area of 83.6 square centimeters (cm2). When required to ensure good germination and healthy plants, a fungicide treatment and/or other chemical or physical treatment was applied. The plants were grown for 8-22 days in a greenhouse with an approximate 14 hr. photoperiod which was maintained at about 29 C during the day and 26 C during the night. Nutrients (Peters Excels 15-5-15 5-Ca 2-Mg and iron chelate) were applied in the irrigation solution as needed and water was added on a regular basis.
Supplemental lighting was provided with overhead metal halide 1000-Watt lamps as necessary. The plants were employed fur testing when they reached the first through fourth true leaf stage.
Treatments consisted of the benzyl ester of 4-amino-3-chloro-5-fluoro-6-(4-chloro-2-fluoro-3-methoxy-phenyl)pyridine-2-carboxylic acid (Compound A), formulated as an SC
(suspension concentrate), an ACCase inhibitor, and a third herbicidal component, each applied alone and in ternary combination. Forms of compound A were applied on an acid equivalent basis.
Forms of compound A (compound of formula I) tested include:

RECTIFIED (RULE 91) - ISA/US

CI
Olt H3e-Compound A Benzyl Ester The ACCase inhibitor component was applied on an active ingredient basis and included eyhalofop-R-butyl formulated as Clincher SF, fenoxaprop-p-ethyl formulated as RiceStar HT, and profoxydim formulated as Aura 20EC. Other herbicidal components were applied on an active ingredient or acid equivalent basis depending on the compound and included penoxsulam formulated as Grasp SC, bentazon sodium formulated as Basagran , trielopyr trimethylammonium (TEA) salt formulated as Grandstand R, bispyribac sodium formulated as Regiment 80WP, imazamox ammonium formulated as Beyond , benzobicyclon, quinclorac formulated as Facet 75DF, glyphosate dimethylammonium (DMA) salt formulated as Durango DMA, glufosinate ammonium formulated as Ignite 280, fentrazamide formulated as an emsulsifiable concentrate (EC), propyrisulfiiron formulated as Zeta One , and indanofan (technical grade material).
Treatment requirements were calculated based upon the rates being tested, the concentration of active ingredient or acid equivalent in the formulation, and a 12 mL
application volume at a rate of 187 Lla.
For treatments comprised of formulated compounds, measured amounts of compounds were placed individually in 25 MI. glass vials and diluted in a volume of 1.25%
(WV) Agri-Dex crop oil concentrate to obtain 12X stock solutions. If a test compound did not dissolve readily, the mixture was warmed and/or sonicated. Application solutions were prepared by adding an appropriate amount of each stock solution (e.g., I mL) and diluted to the appropriate final concentrations with the addition of 9 m.L of an aqueous mixture of 1.25% (v/v) crop oil concentrate so that the final spray solutions contained 1.25% (v/v) crop oil concentrate.
For treatments comprised of formulated and technical compounds, weighed amounts of the technical materials were placed individually in 25 miL glass vials and dissolved in a volume of 97:3 v/v acetone/DMSO to obtain 12X stock solutions, and measured amounts of the formulated compounds were placed individually in 25 mL glass vials and diluted in a SUBSTITUTE SHEET (RULE 26) volume of 1.5% (v/v) crop oil concentrate to obtain 12X stock solutions. If a test compound does not dissolve readily, the mixture was warmed and/or sonicated.
Application solutions were prepared by adding an appropriate amount of each stock solution (e.g., 1 mi.) and diluted to the appropriate final concentrations with the addition of an appropriate amount of an aqueous mixture of 1.5% (v/v) crop oil concentrate so that the final spray solutions contained 1.25% (v/v) crop oil concentrate. As required, additional water and/or 97:3 v/v acetone/DMS0 was added to individual application solutions so that the final acetone and DMSO concentrations of the application solutions being compared were 8.1% and 0.25%, respectively.
All stock solutions and applications solutions were visually inspected for compound compatibility prior to application. Spray solutions were applied to the plant material with an overhead Mandel track sprayer equipped with a 8002E nozzles calibrated to deliver 187 L/ha over an application area of 0.503 m2 at a spray height of 18 inches (46 cm) above average plant canopy height. Control plants were sprayed in the same manner with the solvent blank.
The treated plants and control plants were placed in a greenhouse as described above and watered by sub-irrigation to prevent wash-off of the test compounds. After approximately 3 weeks, the condition of the test plants as compared with that of the untreated plants was determined visually and scored on a scale of 0 to 100 percent where 0 corresponds to no injury or growth inhibition and 100 corresponds to complete kill.
Colby's equation was used to determine the herbicidal effects expected from the mixtures (Colby, S.R.. 1967. Calculation of the synergistic and antagonistic response of herbicide combinations. Weeds 15:20-22.) .
The following equation was used to calculate the expected activity of mixtures containing three active ingredients, A, B, and C:
Expected = A + B + C-((A xB+A xC+B x C)1100) + (A x B x C/10000) A = observed efficacy of active ingredient A at the same concentration as used in the mixture.
B = observed efficacy of active ingredient B at the same concentration as used in the mixture.
C = observed efficacy of active ingredient C at the same concentration as used in the mixture.
The compounds tested, application rates employed, plant species tested, and results are given in Tables 49-62.

SUBSTITUTE SHEET (RULE 26) Table 49. Synergistic Activity of Foliar-Applied Compound A Benzyl Ester, Cyhalofop-Butyl, and Penoxsulam Ternary Herbicidal Compositions on Weed Control in a Rice Cropping System.
Compound Visual Weed Cvhalofop-A Benzyl ' butyl Penoxsulam Control (%) - 21 Ester ' DAA
'PORE
_ gae/ha gai/ha gailha Ohs Exp _ 0 0 _ 8.75 48 . -8 35 8.75 61 56 16 35 8.75 90 66 Table 50. Synergistic Activity of Foliar-Applied Compound A Benzyl Ester, Cyhalofop-Butyl, and Bentazon Ternary Herbicidal Compositions on Weed Control in a Rice Cropping System.
................................
Compound Visual Weed , Cyhalofop- Bentazon A BenzyiControl (%) - 21 butyl sodium Ester DAA
IPOHE
gae/ha gai/ha gae/ha Ohs Exp 2.19 . 0 0 30 -4.38 0 0 38 -Si 0 Si 420 Cl -2.19 35 420 70 67 4.38 35 420 82 71 Compound . Visual Weed Cyhalofop- Bentazon A BenzylControl (%) - 21 butyl sodium Ester DAA

gae/ha .):ai/ha gae/ha Obs Exp 8 0 0 15 - .

.
0 0 420 -- 75 ' -SUBSTITUTE SHEET (RULE 26) [ i 6 I 35 I 420 I 93 I 83J
Table 51. Synergistic Activity of Foliar-.Applied Compound A Benzyl Ester, Cyhalofop-Butyl, and Triclopyr TEA Salt Ternary Herbicidal Compositions on Weed Control in a Rice Cropping System.
Compound Cyhalofop Triclopyr A Benzyl _ butyl TEA Salt Visual Weed Control (%) - 21 DAA
Ester ECIICG ECHCO SCPJIJ
gaellia ' gailha ga cilia Obs Exp Obs Exp Obs Exp 2.19 0 0 5 - 10 - 65 -4.38 0 0 27 - 25 - 96 -0 ; 0 , 17.5 0 - 3 - 43 -2.19 . 35 17.5 35 24 45 45 98 80 4.38 35 17.5 37 41 90 54 100 98 ;
Compound Visual Weed -Cvhalofop Triclopyr A Benzyl ' butyl . Control (%) - 21 TEA Salt Ester DAA
CYPIR
gaelha oailha c: gaellia Obs Exp _ ......_ 0 0 17.5 0 8 35 17.5 100 53 16 35 17.5 100 95 Table 52. Synergistic Activity of Foliar-Applied Compound A Benzyl Ester, Cyhalofop-Butyl, and Bispyribac Sodium Ternary Herbicidal Compositions on Weed Control in a Rice Cropping System.
Compound Cyhalofop- Bispyribac .
A Benzyl Visual Weed Control (%) - 21 DAA
butyl sodium Ester _ IPOHE CYPES
pelha pi/ha gai/ha Obs Exp Obs Exp SUBSTITUTE SHEET (RULE 26) Table 53. Synergistic Activity of Foliar-Applied Compound A Benzyl Ester, Cyhalofop-Butyl, and Imazamox Ammonium Ternary Herbicidal Compositions on Weed Control in a Rice Cropping System.
c ., Compound Visual Weed Cyhalofop- Imaz.amox A Benzyl Control (%) - 21 butyl ammonium Ester DAA
CAPES
gae/ha c,ai/ha :.-: gai/ha Ohs Exp 0 0 12 60 .
o 8 35 12 95 88 Compound Visual Weed Cyhalolop- Irnazamox A Benzyl Control (%) - 21 butyl ammonium Ester DAA
MAHE
gae/ha gai/ha . pc/ha . Ohs Exp 8 0 0 20 - .
0 17.5 0 0 0 0 6 65 - .
8 17.5 6 85 72 Table 54. Synergistic Activity of Foliar-Applied Compound A Benzyl Ester, Cyhalofop-Butyl, and Benzobicyclon Ternary Herbicidal Compositions on Weed Control in a Rice Cropping System, Compound . Visual Weed Cyhap-A Benzyl lofo Benzobicyclon Control (%) -butl Ester y .DAA
. . , ECHCG
. . , ciae/ha szaillia gai/ha Obs Exp -+ +
+
8 0 0 38 - .
0 35 0 20 _ .

SUBSTITUTE SHEET (RULE 26) Compound Visual Weed Cyhalofop-A Benzyl ' Benzobicyclon Control (%) - 21 butyl Ester DAA
IPOHE
, gae/ha gailha gal/ha Obs Exp 8 , 0 0 10 8 . 35 200 78 60 Table 55. Synergistic Activity of Foliar-Applied Compound A Benzyl Ester, Cybalofop-Butyl, an.d Quinclorac Ternary Herbicidal Compositions on Weed Control in a Rice Cropping System.
____________ Compound Cvhal f o A Benzyl - " - Quinclorac Visual Weed Control (%) -21 DAA
butyl Ester _______________________________ , ..........
ECHCG CYPES
gae/ha gaitha gai/ha Obs Exp Obs Exp 8 35 280 92 55 . 85 70 Table 56. Synergistic Activity of Foliar-Applied Compound A Benzyl Ester, Cyhalofop-Butyl, and Glyphosate Dimethylammonium (DMA) Salt Ternary Herbicidal Compositions on Weed Control in a Rice Cropping System.
Compound Visual Weed A Benzyl CYhal f P- Glyphosate Control ( /0) - 21 butyl DMA
. Ester DAA
LEECH
gaelha gal/ha gai/ha Obs Exp 16 0 0 25 - .

Compound Visual Weed D
Cvhal f . - - Glvohosat-A Benzyl - Control ( /0) - 21 butyl DMA
Ester DAA

SUBSTITUTE SHEET (RULE 26) ECHCG
gae/ha gailha gae/ha Obs Exp 0 17.5 0 33 -8 17.5 105 83 71 Table 57. Synergistic Activity of Foliar-Applied Compound A Benzyl Ester, Cyhalofop-Butyl, and Glufosinate Ammonium Ternary Herbicidal Compositions on Weed Control in a Rice Cropping System.
CompoundVisual Weed -Cvhalofon Glufosin ate .
A Benzyl - = Control (%) - 21 butyl ammonium Ester DAA
ECHCO
gae/ha gaitha gal/ha Obs Exp Table 58. Synergistic Activity of Foliar-Applied Compound A Benzyl Ester, Cyhalofop-Butyl, and Fentrazamide Ternary Herbicidal Compositions on Weed Control in a Rice Cropping System.

Compound Cvhal = f (ID-A Benzyl - Fentrazamide Visual Weed Control (%) - 22 DAA
butyl Ester ECHCG ECHOR
, _________________________________________________ gae/ha gai/ha gal/ha Obs Exp Obs Exp -0 17.5 0 0 - 0 - .

0 0 33.75 0 - 3 -0 0 , 67.5 0 i - 0 -8 17.5 33.75 40 40 25 16 8 17.5 67.5 67 40 52 13 8 ' 35 33.75 48 47 63 29 8 35 67.5 65 47 55 26 i 16 17.5 33.75 83 58 60 42 16 17.5 67.5 80 58 82 40 SUBSTITUTE SHEET (RULE 26) 16 35 33.75 -- 92 63 -- 80 51 ' --------------------------------------------16 35 67.5 87 63 87 49 , Table 59. Synergistic Activity of Foliar-Applied Compound A Benzyl Ester, Cyhalofop-Butyl, and Propyrisulfuron Ternary Herbicidal Compositions on Weed Control in a Rice Cropping System, c ., Compound-Visual Weed Cyhalofop-A Benzyl Propyri butyl sulfuron Control (%) -Ester µ 22 DAA
ECHOR
gae/ha gai/ha gailha Ohs Exp .._.

0 0 22.5 55 8 35 72.5 78 67 Table 60. Synergistic Activity of Foliar-Applied Compound A Benzyl Ester, Fenoxaprop-p-Ethyl -t- Isoxadifen-ethyl, and Penoxsulam Ternary Herbicidal Compositions on Weed Control in a Rice Cropping System.
Fenoxaprop- -Compound-Visual Weed p-ethyl -I
A Betrzyl Penoxsulam Control (%) - 22 Isoxadifen-Ester DAA
, ethyl ECHOR
gae/ha 0-ai/ha :.-, gai/h a Ohs Exp 8 0 0 25 - .

0 4.38 0 45 0 8.75 0 53 -0 0 4.38 0 -8 4,38 4.38 73 59 8 8.75 . 4.38 (7,.-,L, 16 4.38 4.38 82 64 16 8.75 4.38 87 70 Fenoxaprop-Compound Visual Weed p-ethvl +
A Benzyl Penoxsulam ' Control (%) - 22 lsoxadifen-Ester DAA
ethyl , CYPIR

SUBSTITUTE SHEET (RULE 26) gae/h.a gailha gailha. Ohs Exp 0 4.38 0 50 -0 0 4.38 0 -0 0 8.75 0 _ 8 4.38 438 , -- 83 68 8 4.38 8.75 88 68 Table 61. Synergistic Activity of Foliar-Applied Compound A Benzyl Ester, Profoxydim, and Penoxsulam Ternary Herbicidal Compositions on Weed Control in a Rice Cropping System.
Compound Visual Weed A Benzyl Penoxsulam Profoxydim Control (c,v0) - 22 Ester DAA
ECHOR
.
gae/ha gai/hagai/ha Ohs Exp .

0 4.38 0 45 _ 0 0 , 3.12 0 8 4.38 3.17 16 4038 3.12 70 64 Compound Visual Weed A Benzyl Penoxsulam Prol-bxydim Control (%) - 22 Ester DAA
CYP1R.
gae/ha gai/ha gai/ha , Obs Exp , 8 0, 0 37 0 4.38 0 50 - .
0 0 3.12 0 -0 0 . 6.25 0 , -8 4038 3.12 87 ... 68 ..
8 4.38 6.25 87 68 Table 62. Synergistic Activity of Foliar-Applied Compound A Benzyl Ester, Cyhalefop-butyl, and ludanofan Ternary Herbicidal Compositions on Weed Control in a Rice Cropping System.
Compound Visual Weed Cyhalofop-A Benzyl = Indanofan Control (1)/0) - 22 butyl Ester DAA

SUBSTITUTE SHEET (RULE 26) LEFCH
gae/ha gailha Yaitha Obs Exp o 35 0 70 0 0 72.5 30 8 35 72.5 95 85 CYPES Operus esculentus L. nutsedge, yellow CYPIR Cyperus iria L. flatsedge, rice ECHCG Echinochloa crusgalli (L.) Beauv. bamyardgrass ECHCO .Echinochloa colona (L.) Link junglerice ECHOR Echinochloa oryzoides (Ard.) Fritsch early watergrass IPOHE Ipomoea hederacea jacq. morningglory, ivyleaf LEFCH Leptochloa chinensis (L.) Nees sprangletop, Chinese SCPJU Schoenoplectus juncoldes (Roxb.) Palla bulrush, Japanese gae/ha = grams acid equivalent per hectare gal/ha = grams active ingredient per hectare Obs = observed value Exp = expected value as calculated by Colby's equation DAA = days after application Example VI. Evaluation of In-Water Applied Ternary Herbicidal Mixtures for Weed Control in Transplanted Paddy Rice Weed seeds or nutlets of the desired test plant species were planted in puddled soil (mud) prepared by mixing a shredded, non-sterilized mineral soil (50.5 percent silt, 25.5 percent clay, and 24 percent sand, with a pH of about 7.6 and an organic matter content of about 2.9 percent) and water at a 1:1 volumetric ratio. The prepared mud was dispensed in 365 mL aliquots into 16-ounce (oz.) non-perforated plastic pots with a surface area of 86.59 square centimeters (cm2) leaving a headspace of 3 centimeters (cm) in each pot. Mud was allowed to dry overnight prior to planting or transplanting. Rice seeds were planted in Sun Gro MetroMix 306 planting mixture, which typically has a pH of 6.0 to 6.8 and an organic matter content of about 30 percent, in plastic plug trays. Seedlings at the second or third leaf stage of growth were transplanted into 860 rriL of mud contained in 32-oz. non-perforated plastic pots with a surface area of 86.59 cm2 4 days prior to herbicide application. The paddy SUBSTITUTE SHEET (RULE 26) was created by filling the headspace of the pots with 2.5 to 3 cm of water.
When required to ensure good germination and healthy plants, a fungicide treatment and/or other chemical or physical treatment was applied. The plants were grown for 4-22 days in a greenhouse with an approximate 14 hr. photoperiod which was maintained at about 29 C during the day and 26 C during the night. Nutrients were added as Osmocote (19:6:12, N:P:K +
minor nutrients) at 2 g per 16-oz. pot and 4 g per 32-oz. pot. Water was added on a regular basis to maintain the paddy flood, and supplemental lighting was provided with overhead metal halide 1000-Watt lamps as necessary. The plants were employed for testing when they reached the first through fourth true leaf stage.
Treatments consisted of the ben71 ester of 4-amino-3-chloro-5-fluoro-6-(4-chloro-2-fluoro-3-methoxy-phenyl)pyridine-2-carboxylic acid (Compound A), formulated as an SC
(suspension concentrate), an ACCase inhibitor herbicide, and a third herbicidal component, each applied alone and in ternary combination. Forms of compound A were applied on an acid equivalent basis.
Forms of compound A (compound of formula 1) tested include:

,CI
I
WThr 1-13( Compound A Benzyl Ester The ACCase inhibitor component was applied on an active ingredient basis and included cyhalofop-R-butyl formulated as Clincher G and metamifop formulated as Metamifop EC. Other herbicidal components were applied on an active ingredient or acid equivalent basis depending on the compound and included penoxsulam formulated as Grasp SC, bentazon sodium formulated as Basagran , triclopyr trimethylammonium (TEA) salt formulated as Grandstand R, benzobicyclon formulated as Benzobicyclon, benfuresate formulated as Full Slot WG, pyraclonil formulated as Pyraclon Flowable, mefenacet (technical grade material), and pretilachlor (technical grade material).
Treatment requirements for each compound or herbicidal component were calculated based upon the rates being tested, the concentration of active ingredient or acid equivalent in RECTIFIED (RULE 91) - ISA/US

the formulation, an application volume of 1 mL per component per pot, and an application area of 86.59 cm2 per pot.
For formulated compounds, a measured amount was placed in an individual 100 or 200 mL glass vial and was dissolved in a volume of 1.25% (v/v) Agri-Dex crop oil concentrate to obtain application solutions. If the test compound did not dissolve readily, the mixture was warmed and/or sonicated.
For technical grade compounds, a weighed amount was placed in an individual 100 to 200 mL glass vial and was dissolved in a volume of acetone to obtain concentrated stock solutions. If the test compound did not dissolve readily, the mixture was warmed and/or sonicated. The concentrated stock solutions obtained were diluted with an equivalent volume of an aqueous mixture containing 2.5% (v/v) oil concentrate so that the final application solutions contained 1.25% (v/v) crop oil concentrate.
Applications were made by injecting with a pipetter appropriate amounts of the application solutions, into the aqueous layer of the paddy. Control plants were treated in the same manner with the solvent blank. Applications were made so that all treated plant material received the same concentrations of acetone and crop oil concentrate.
The treated plants and control plants were placed in a greenhouse as described above and water was added as needed to maintain a paddy flood. After approximately 3 weeks the condition of the test plants as compared with that of the untreated plants was determined visually and scored on a scale of 0 to 100 percent where 0 corresponds to no injury or growth inhibition and 100 corresponds to complete kill.
Colby's equation was used to determine the herbicidal effects expected from the mixtures (Colby, S.R. 1967. Calculation of the synergistic and antagonistic response of herbicide combinations. Weeds 15:20-22.) .
The following equation was used to calculate the expected activity of mixtures containing three active ingredients, A, B, and C:
Expected = A B C-((A x B A x C B x c)/loo) + (A x B x C/10000) A = observed efficacy of active ingredient A at the same concentration as used in the mixture.
B = observed efficacy of active ingredient B at the same concentration as used in the mixture.
C = observed efficacy of active ingredient C at the same concentration as used in the mixture.

SUBSTITUTE SHEET (RULE 26) The compounds tested, application rates employed, plant species tested, and results are given in Tables 63-71 .
Table 63. Synergistic Activity of In-Water Applications of Compound A Benzyl Ester, Cyhalofop-butyl, and Penoxsulam Ternary Herbicidal Compositions on Weed Control in a Rice Cropping System.
Compound Visual Weed Control (%) - 21 DAA
Cvhalofop-A Benzyl ' Penoxsulam butyl Ester .
-MIMI ECHCG
, gae/ha gai/ha c,aiiha Ohs Exp Ohs Exp 1.09 0 0 8 _ - 0 -+
2.19 0 0 33 7 -0 225 0 .) .),, +

0 0 1.25 33 - 17 -.
1.09 225- 1.25 70 59 28 17 2.19 22.5 1.25 95 70 58 , 22 _ 1.09 45 1.25 65 _ 39 45 19 +
2.19 45 1.25 87 56 87 75 Compound Visual Weed A Benzyl Cvhalofop- l'enoxsulam Control (%) - 21 butyl Ester. . DAA
ECHCG
gaelha 1.)õ,ai/ha gailha Ohs Exp 8 0 0 , 45 - , 16 0 0 99 - , 0 0 2.5 55 -4 45 2.5 85 76 8 45 ').,; 100 83 16 45 2,5 100 100 Compound Visual Weed A Benzyl Cvhalofop- 1)enoxsulain Control (%) - 21 butyl EsterDAA
. .
CYPRO
tzae/ha -7,'111 gailha Ohs g.a, a Exp 2.19 0 0 0 -0 22.5 0 0 -SUBSTITUTE SHEET (RULE 26) 0 . 0 1.25 0 -2.19 22.5 1.25 23 0 2.19 45 1.25 28 0 Compound Visual Weed Cvl '1 f A Benzyl ' id ."n - Penoxsulam Control ( ,10) - 24 butyl Ester DAA
CY PRO
gaelha gal/ha r., . gailha Obs Exp 8 . 0 0 60 -0 0 2.5 0 ----. 0 0 5 0 -4 90 1.5 60 40 8 90 2.5 55 60 16 90 2.5 90 85 4 180 2.5 60 40 8 180 2.5 90 60 16 180 2.5 100 85 Compound vh Visual Weed Calofon-A Benzyl ' 'butyl . Penoxsulain Control (%) - 24 Ester DAA
FRAM!
5.5.ae/ha gal/ha gailha Obs Exp 0 0 2.5 60 -4 90 1.5 78 60 8 90 2.5 95 80 16 90 2.5 100 72 4 180 2.5 90 68 8 180 2.5 80 84 SUBSTITUTE SHEET (RULE 261) 16 I 180 1 2.5 1 99 I 78 I
Compoundõ ,_'_,"õ. Visual Weed A Benzvl uY"1 P-Penoxsulam Control (%) - 24 butyl Ester DAA
SCP NIA
gae/ha gai/ha _gai/ha Obs Exp , 8 0 0 0 - .

, , 8 180 5 70 30 .

Table 64. Synergistic Activity of In- Water Applications of Compound A Benzyl Ester, Cyhalofop-butyl, and Beniazon Sodium Ternary Herbicidal Compositions on Weed Control in a Rice Cropping System, Compound,,,,,,õ ,, Visual Weed k., namop- Bentazon A Benzyl i Control (/o) - 21 I buty Sodum Ester DAA .
ECHCG
gae/ha gai/ha gae/ha Ohs Exp , 1.09 , 0 0 0 -' 2.19 0 0 / -0 22.5 , 0 0 -1.09 , 22.5 , 210 20 , 0 2.19 22,5 210 17 7 1.09 45 , 210 13 3 2.19 45 210 77 10 ............ , ...................................
Compound Visual Weed Cyhalofop- Bentazon . , . , A Benzyl Control 04) - z.1 butyl Sodium Ester DAA
ECHCCi-gae/ha gai/ha gae/ha Ohs Exp 4 0 0 25 - .
8 0 0 45 , -, SUBSTITUTE SHEET (RULE 26) ______ 0 0 420 15 Compound Visual Weed Cvhalofu- p- Bentazon A Benzyl - butyl.' Control (.%) - 21 Sodium Ester DAA

gaelha gai/ha gaelha Obs Exp 1.09 0 0 8 -2.19 0 0 33 -...... ....
1.09 45 210 33 24 . 2.19 45 210 68 44 Compound Visual Weed Cyhalofop- Bentazon A Benzyl Control (%) - 21 butyl Sodium DAA
Ester , , .
FIMMI
gaelha gai/ha gae/ha Obs Exp 0 . 22.5 0 0 ------0 45 0 0 - , 4 22.5 420 93 73 Table 65. Synergistic Activity of In-Water Applications of Compound A Benzyl Ester, Cyhalofop-butyl, and Tiiclopyr Trimethylammonium (TEA) Salt Ternary Herbicidal Compositions on Weed Control in a Rice Cropping System.
Compound 'Visual Weed 41'1op- ric C f T = 1 ) d 0 opyr A Benzyl Control e/o) - 21 butyl TEA
Ester DAA
ECHCG
gaelha gaillia Gaelha ,.:, Obs Exp 1.09 0 0 0 -. 2.19 0 0 7 -0 22.5 0 0 -0 0 17.5 0 -SUBSTITUTE SHEET (RULE 26) ________ 1.09 22.5 17.5 ... 25 0 2.19 22.5 , 17.5 48 7 1.09 45 , 17.5 37 3 _.
2.19 45 17.5 48 10 Compound Visual Weed Cvhalofon- Thelon/
A Benzyl - . . . - Control (%) - 21 butyl TEA
Ester DAA
ECHCG
ne/ha gal/ha --gailha Obs Exp ,,, .
4 . 0 0 25 -_ ______ 4 45 35 100 48 8 45 35 100 62 , Compound Visual Weed Cyhalofop- Triclopyr A Benzyl Control (%) - 21 butyl TEA
Ester DAA

uae/ha gal/ha gae/ha Obs Exp :-...
2.19 . 0 0 77 -0 //.5 0 0 -0 0 17.5 8 2.19 22.5 17.5 93 79 ...._ 2.19 45 17.5 88 79 Table 66. Synergistic Activity of in-Water Applications of Compound A Benzyl Ester, Cyhalofop-butyl, and Benfuresate Ternary Herbicidal Compositions on Weed Control in a Rice Cropping System.
Compound Visual Weed -D
Cvhal f A Benzyl - . Benfuresate Control (.13/0) -butyl Ester DAA
ECHCG
gae/ha gaitha . gal/ha Obs Exp 0 . 45 0 30 -SUBSTITUTE SHEET (RULE 26) Table 67. Synergistic Activity of In-Water Applications of Compound A Bcnryl Ester, Cyhalofop-butyl, and Benzobicyclon Ternary Herbicidal Compositions on Weed Control in a Rice Cropping System.
Compound Visual Weed Cvhalofop-A Benzyl Benzobicyclon Control (0/0) - 21 butyl Ester DAA
, ECHCCi gae/ha gai/ha gaidia Ohs , Exp 4 0 0 25 - .
--, +
+
0 0 100 20 - .

Compound Visual Weed cyhrs_ A Benzyl atofo I' Benzobicyclon Control (%) -24 bl Ester tit DAA
ECHOR
, _________________________________________________ 0-aellia gai/ha c,aiiha Ohs Exp -, 0 0 25 10 _ -, ---------------------------, Compound Visual Weed Cvhalofop-A Benzyl butyl Benzobicyclon Control (%) - 24 Ester DAA
FININIE
gae/ha gal/ha ,.., , gaillta Ohs Exp 4 0 0 0 - .
' -8 0 0 ------ 50 _ ., SUBSTITUTE SHEET (RULE 26) 16 0 0 30 . ----0 0 50 68 , - , Table 68. Synergistic Activity of In-Water Applications of Compound A Benzyl Ester, Cyhalofop-butyl, and Pyracionil Ternary Herbicidal Compositions on Weed Control in a Rice Cropping System, Compound Visual Weed Cylialofop-A Benzyl = Pyraclonil Control (%) - 21 Ester butyl DAA
ECHCG
gae/ha , gai/ha , gai/ha Ohs , Exp 16 0 0 99 - .

0 0 22,5 30 4 45 22.5 , 100 63 .
8 45 , 22.5 100 7.1 16 45 22.5 100 100 Compound Visual Weed Cyhalofop-A Benzyl Pyraclonii Control (%) - 21 butyl Ester DAA
SCPMA
aae/ha gai/ha gai/ha Ohs Exp 0 22.5 0 0 0 0 22.5 78 4 .2.2.5 22,5 83 78 8 22.5 .z. -1-.z.1 ....,.;

16 22.5 22,5 --- 93 ---- 78 4 45 22.5 ---- 95 --- 78 --8 45 22.5 98 78 16 45 22,5 90 78 SUBSTITUTE SHEET (RULE 26) Table 69. Synergistic Activity of In-Water Applications of Compound A Benzyl Ester, Cyhalofop-butyl, and Mefenacet Ternary Herbicidal Compositions on Weed Control in a Rice Cropping System.
Compound Cvhalofop Visual Weed A Benzyl - . - - Mefenacet Control (A) - 21 b Ester utyl DAA
CYPRO
aae/ha tz gailha gailta Obs Exp 8 0 0 33 - , Table 70. Synergistic Activity of In-Water Applications of Compound A Benzyl Ester, Cyhalofop-butyl, and Pretilachlor.
Compound Cv Visual Weed halofon A Benzyl - . - - Pretilachlor Control (%) - 21 b Ester utyl DAA
CYPRO
eae/ha gaiiha gailta Obs Exp SUBSTITUTE SHEET (RULE 26) Table 71. Synergistic Activity of in-Water Applications of Compound A Benzyl Ester, Metatnifop, and Pertoxsulain Ternary Herbicidal Compositions on Weed Control in a Rice Cropping System.
Compound Visual Weed A Benzyl Penoxsulam Metamifop Control (%) - 24 Ester DAA
ECHOR
tzae/ha gai/ha gailha Ohs Exp 8 5 50 100 7,4 CYPRO Cyperus rotundus U nutsedge, purple ECHCG Echinochloa crusgalli (L.) Beauv. barnyardgrass ECHOR Echinochloa ogzoides (Ard.) Fritsch watergrass, early FIMMI Fimbristylis miliacea (L.) Vahl fringerush, globe SCRIU Schoenoplectus juncoides (Roxb,) Palla bulrush, Japanese SCPMA Bolboschoenus maritimus (L.) Palla or Schoenoplectus maritimus (L.) Lye elubrush, sea gaeiha -= grams acid equivalent per hectare 1.5 gana = grains active ingredient per hectare Obs = observed value Exp = expected value as calculated by Colby's equation DAA = days after application SUBSTITUTE SHEET (RULE 26)

Claims (14)

WHAT IS CLAIMED IS:

1. A synergistic herbicidal composition comprising a herbicidally effective amount of (a) a compound of the formula (I) or an agriculturally acceptable salt or ester thereof and (b) an ACCase inhibitor.

2. The composition of claim 1, wherein (a) is the compound of formula (I), a C1-4 alkyl ester of the compound of formula (I), or a benzyl ester of the compound of formula (I).

3. The composition of any of claims 1-2, wherein (b) is at least one compound, or an agriculturally acceptable salt, carboxylic acid, carboxylate salt, or ester thereof, selected from the group consisting of: clethodim, clodinafop-propargyl, cyhalofop-R-butyl, diclofop-methyl, fenoxaprop-P-ethyl, fluazifop-P-butyl, haloxyfop-R-methyl, metamifop, pinoxaden, profoxydim, quizalofop-P-ethyl, sethoxydim, and tralkoxydim.

4. The composition of any of claims 1-3, further comprising an agriculturally acceptable adjuvant or carrier.

5. The composition of any of claims 1-4, further comprising a herbicide safener.

6. A method of controlling undesirable vegetation which comprises contacting the vegetation or the locus thereof with or applying to the soil or water to prevent the emergence or growth of vegetation a herbicidally effective amount of (a) a compound of the formula (I) or an agriculturally acceptable salt or ester thereof and (b) an ACCase inhibitor

7. The method of claim 6, wherein (a) is the compound of formula (I), a C1-4 alkyl ester of the compound of formula (I), or a benzyl ester of the compound of formula (I).

8. The method of any of claims 6-7, wherein (b) is at least one compound, or an agriculturally acceptable salt, carboxylic acid, carboxylate salt, or ester thereof, selected from the group consisting of: clethodim, clodinafop-propargyl, cyhalofop-R-butyl, diclofop-methyl, fenoxaprop-P-ethyl, fluazifop-P-butyl, haloxyfop-R-methyl, metamifop, pinoxaden, profoxydim, quizalofop-P-ethyl, sethoxydim, and tralkoxydim.

9. The method of any of claims 6-8, wherein the undesirable vegetation is controlled in direct-seeded, water-seeded and transplanted rice, cereals, wheat, barley, oats, rye, sorghum, corn/maize, sugarcane, sunflower, oilseed rape, canola, sugar beet, soybean, cotton, pineapple, pastures, grasslands, rangelands, fallowland, turf, tree and vine orchards, aquatics, industrial vegetation management (IVM) or rights of way (ROW).

10. The method of any of claims 6-9, wherein the (a) and (b) are applied pre-emergently to the weed or the crop.

11. The method of any of claims 6-10, wherein the undesirable vegetation is controlled in glyphosate-, 5-enolpyruvylshikimate-3-phosphate (EPSP) synthase inhibitor-, glufosinate-, glutamine synthetase inhibitor-, dicamba-, phenoxy auxin-, pyridyloxy auxin-, synthetic auxin-, auxin transport inhibitor-, aryloxyphenoxypropionate-, cyclohexanedione-, phenylpyrazoline-, acetyl CoA carboxylase (ACCase) inhibitor-. imidazolinone-, sulfonylurea-, pyrimidinylthiobenzoate-, triazolopyrimidine-, sulfonylaminocarbonyltriazolinone-, acetolactate synthase (ALS) or acetohydroxy acid synthase (AHAS) inhibitors-, 4-hydroxyphenyl-pyruvate dioxygenase (HPPD) phytoene desaturase inhibitor-, carotenoid biosynthesis inhibitor-, protoporphyrinogen oxidase (PPO) inhibitor-, cellulose biosynthesis inhibitor-, mitosis inhibitor-, microtubule inhibitor-, very long chain fatty acid inhibitor-, fatty acid and lipid biosynthesis inhibitor-, photosystem I inhibitor-, photosystem II inhibitor-, triazine-, or bromoxynil-tolerant crops.

12. The method of claim 11, wherein the tolerant crop possesses multiple or stacked traits conferring tolerance to multiple herbicides or multiple modes of action.

13. The method of any of claims 6-12, wherein the undesirable vegetation comprises a herbicide resistant or tolerant weed.

14. The composition of any of claims 1-5, further comprising at least one compound selected tiorn the group consisting of penoxsulam, bentazon-sodium, triclopyr, bispyribac-sodium, imazamox, benzobicyclon, quinclorac, glyphosate, glufosinate, benfuresate, fentrazamide, indanofan, ipfencarbazone, mefenacet, oxazichlomefone, pretilachlor, propyrisulfuron, pyraclonil, pyriftalid, and pyrimisulfan, or an agriculturally acceptable salt, carboxylic acid, carboxylate salt, or ester thereof, in combination as a synergistic 3 way/ternary mixture.